NPASS Compound

Structure

CID60408 OpenBabel06191715392D 21 23 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 16 17 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.27
Volume:	580.367
LogP:	5.633
LogD:	4.389
LogS:	-5.641
# Rotatable Bonds:	19
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	2.859
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.61
MDCK Permeability:	1.952955426531844e-05
Pgp-inhibitor:	0.793
Pgp-substrate:	0.183
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	98.7748794555664%
Volume Distribution (VD):	0.487
Pgp-substrate:	1.0947152376174927%

ADMET: Metabolism

CYP1A2-inhibitor:	0.286
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.91
CYP2C19-substrate:	0.276
CYP2C9-inhibitor:	0.784
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.41
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.829
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	11.698
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.443
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.124
Respiratory Toxicity:	0.419

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC60408

Natural Product ID:	NPC60408
*Common Name:**	[(1R,4As,10Ar)-1,4A-Dimethyl-7-Propan-2-Yl-2,3,4,9,10,10A-Hexahydrophenanthren-1-Yl]Methanamine
IUPAC Name:	[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine
Synonyms:
Standard InCHIKey:	JVVXZOOGOGPDRZ-SLFFLAALSA-N
Standard InCHI:	InChI=1S/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/t18-,19-,20+/m0/s1
SMILES:	CC(C)c1ccc2c(CC[C@H]3[C@@](C)(CCC[C@]23C)CN)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL70488
PubChem CID:	62034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22060189]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[22723874]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23371463]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flowers	Lasa, China	n.a.	PMID[24621197]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27748595]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Bud	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	6
IC50	20
Others	39
Potency	6

Activity Type	# Activity
Cell Line	38
Individual Protein	5
Organism	21
Others	6
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[528562]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[528562]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[528562]
NPT3508	Cell Line	EJ	Homo sapiens	Activity	=	6.16	%	PMID[528563]
NPT3508	Cell Line	EJ	Homo sapiens	Activity	=	87.9	%	PMID[528563]
NPT3508	Cell Line	EJ	Homo sapiens	Activity	=	5.85	%	PMID[528563]
NPT3508	Cell Line	EJ	Homo sapiens	Activity	=	0.13	%	PMID[528563]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	4850.0	nM	PMID[528563]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7680.0	nM	PMID[528563]
NPT3508	Cell Line	EJ	Homo sapiens	IC50	=	4820.0	nM	PMID[528563]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	7880.0	nM	PMID[528563]
NPT2295	Cell Line	5637	Homo sapiens	IC50	=	8700.0	nM	PMID[528563]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	6500.0	nM	PMID[528566]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2020.0	nM	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2560.0	nM	PMID[528568]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	19450.0	nM	PMID[528568]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5020.0	nM	PMID[528568]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	1270.0	nM	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	22.94	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	15.46	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	0.69	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	60.91	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	44.79	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	22.98	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	0.24	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	31.99	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	91.91	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	0.7	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	0.0	%	PMID[528568]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	1.4	%	PMID[528568]
NPT886	Cell Line	NIH3T3	Mus musculus	EC50	=	2400.0	nM	PMID[528569]
NPT763	Cell Line	SW-1736	Homo sapiens	EC50	=	4200.0	nM	PMID[528569]
NPT139	Cell Line	HT-29	Homo sapiens	EC50	=	2100.0	nM	PMID[528569]
NPT1216	Cell Line	FaDu	Homo sapiens	EC50	=	3900.0	nM	PMID[528569]
NPT179	Cell Line	A2780	Homo sapiens	EC50	=	3800.0	nM	PMID[528569]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	3000.0	nM	PMID[528569]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	1270.0	nM	PMID[528570]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5020.0	nM	PMID[528570]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	19450.0	nM	PMID[528570]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2560.0	nM	PMID[528570]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2020.0	nM	PMID[528570]
NPT2826	Protein Family	Pyruvate dehydrogenase kinase	Homo sapiens	IC50	=	9500.0	nM	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	18.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	-1.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	11.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	-4.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	2.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	19.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	30.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	28.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	22.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	26.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	36.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	47.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	68.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	69.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	65.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	85.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	86.0	%	PMID[528561]
NPT32	Organism	Mus musculus	Mus musculus	Efficacy	=	90.0	%	PMID[528561]
NPT2	Others	Unspecified		IC50	n.a.	80000.0	nM	PMID[528562]
NPT2	Others	Unspecified		Potency	n.a.	4466.8	nM	PMID[528562]
NPT2	Others	Unspecified		IC50	n.a.	100000.0	nM	PMID[528562]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[528562]
NPT27	Others	Unspecified		Activity	=	17.88	%	PMID[528563]
NPT633	Organism	Leishmania donovani	Leishmania donovani	GI	=	68.7	%	PMID[528566]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	7400.0	nM	PMID[528566]
NPT2	Others	Unspecified		Ratio IC50	=	1.0	n.a.	PMID[528566]
NPT32	Organism	Mus musculus	Mus musculus	CC50	=	14500.0	nM	PMID[528567]
NPT2	Others	Unspecified		Ratio EC50	=	0.8	n.a.	PMID[528569]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC60408 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	2603
0.2-0.3	10060
0.3-0.4	21122
0.4-0.5	7167
0.5-0.6	1096
0.6-0.7	186
0.7-0.8	59
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8765	High Similarity	NPC3190
0.8765	High Similarity	NPC249018
0.8554	High Similarity	NPC159661
0.8272	Intermediate Similarity	NPC54269
0.8072	Intermediate Similarity	NPC276699
0.7882	Intermediate Similarity	NPC290638
0.7865	Intermediate Similarity	NPC133162
0.7857	Intermediate Similarity	NPC307195
0.7816	Intermediate Similarity	NPC315216
0.7738	Intermediate Similarity	NPC258492
0.7738	Intermediate Similarity	NPC96835
0.7711	Intermediate Similarity	NPC1008
0.7711	Intermediate Similarity	NPC135433
0.7711	Intermediate Similarity	NPC226999
0.7711	Intermediate Similarity	NPC280135
0.7711	Intermediate Similarity	NPC158028
0.7711	Intermediate Similarity	NPC39799
0.7711	Intermediate Similarity	NPC87099
0.7711	Intermediate Similarity	NPC193578
0.7654	Intermediate Similarity	NPC6107
0.7634	Intermediate Similarity	NPC298115
0.759	Intermediate Similarity	NPC229235
0.759	Intermediate Similarity	NPC72670
0.7586	Intermediate Similarity	NPC245896
0.7586	Intermediate Similarity	NPC66270
0.7576	Intermediate Similarity	NPC474582
0.7558	Intermediate Similarity	NPC110264
0.7531	Intermediate Similarity	NPC289915
0.7531	Intermediate Similarity	NPC178527
0.7531	Intermediate Similarity	NPC113837
0.7529	Intermediate Similarity	NPC122327
0.7529	Intermediate Similarity	NPC113000
0.7529	Intermediate Similarity	NPC112609
0.7474	Intermediate Similarity	NPC220596
0.7474	Intermediate Similarity	NPC125226
0.747	Intermediate Similarity	NPC139416
0.747	Intermediate Similarity	NPC246822
0.747	Intermediate Similarity	NPC213570
0.7423	Intermediate Similarity	NPC329430
0.7416	Intermediate Similarity	NPC50063
0.7407	Intermediate Similarity	NPC32312
0.7407	Intermediate Similarity	NPC155172
0.7407	Intermediate Similarity	NPC198023
0.7363	Intermediate Similarity	NPC119677
0.7356	Intermediate Similarity	NPC139658
0.7327	Intermediate Similarity	NPC239854
0.7292	Intermediate Similarity	NPC470926
0.7284	Intermediate Similarity	NPC45756
0.7284	Intermediate Similarity	NPC88566
0.7282	Intermediate Similarity	NPC474695
0.7273	Intermediate Similarity	NPC98269
0.7273	Intermediate Similarity	NPC325662
0.7229	Intermediate Similarity	NPC267443
0.7191	Intermediate Similarity	NPC255345
0.7176	Intermediate Similarity	NPC219246
0.7176	Intermediate Similarity	NPC251490
0.7172	Intermediate Similarity	NPC185208
0.7172	Intermediate Similarity	NPC219573
0.716	Intermediate Similarity	NPC29680
0.716	Intermediate Similarity	NPC71009
0.7128	Intermediate Similarity	NPC258046
0.71	Intermediate Similarity	NPC324602
0.7097	Intermediate Similarity	NPC169016
0.7037	Intermediate Similarity	NPC310758
0.7037	Intermediate Similarity	NPC135924
0.7037	Intermediate Similarity	NPC54368
0.7037	Intermediate Similarity	NPC210849
0.7037	Intermediate Similarity	NPC150196
0.7037	Intermediate Similarity	NPC248705
0.7037	Intermediate Similarity	NPC238023
0.7011	Intermediate Similarity	NPC1901
0.7	Intermediate Similarity	NPC12857
0.6989	Remote Similarity	NPC104070
0.6988	Remote Similarity	NPC291066
0.6961	Remote Similarity	NPC221825
0.6957	Remote Similarity	NPC242628
0.6957	Remote Similarity	NPC231986
0.6951	Remote Similarity	NPC22786
0.6931	Remote Similarity	NPC239185
0.6914	Remote Similarity	NPC147062
0.6893	Remote Similarity	NPC128248
0.6893	Remote Similarity	NPC136810
0.6893	Remote Similarity	NPC133809
0.6893	Remote Similarity	NPC476993
0.6869	Remote Similarity	NPC323420
0.6867	Remote Similarity	NPC113670
0.6863	Remote Similarity	NPC134882
0.686	Remote Similarity	NPC200936
0.6837	Remote Similarity	NPC26224
0.6829	Remote Similarity	NPC246588
0.6818	Remote Similarity	NPC244738
0.679	Remote Similarity	NPC8235
0.679	Remote Similarity	NPC64270
0.6782	Remote Similarity	NPC263385
0.6778	Remote Similarity	NPC271642
0.6765	Remote Similarity	NPC265220
0.6765	Remote Similarity	NPC226041
0.6762	Remote Similarity	NPC19856
0.6747	Remote Similarity	NPC66517
0.6737	Remote Similarity	NPC267704
0.6731	Remote Similarity	NPC109514
0.6699	Remote Similarity	NPC75724
0.6698	Remote Similarity	NPC56168
0.6696	Remote Similarity	NPC246904
0.6667	Remote Similarity	NPC98976
0.6667	Remote Similarity	NPC65873
0.6667	Remote Similarity	NPC212114
0.6667	Remote Similarity	NPC120441
0.6667	Remote Similarity	NPC300345
0.6667	Remote Similarity	NPC21211
0.6637	Remote Similarity	NPC473573
0.6636	Remote Similarity	NPC471186
0.6636	Remote Similarity	NPC243601
0.6633	Remote Similarity	NPC30445
0.6612	Remote Similarity	NPC40488
0.6609	Remote Similarity	NPC320656
0.6598	Remote Similarity	NPC203076
0.6585	Remote Similarity	NPC114327
0.6585	Remote Similarity	NPC36357
0.6574	Remote Similarity	NPC94751
0.6574	Remote Similarity	NPC142326
0.6571	Remote Similarity	NPC225079
0.6569	Remote Similarity	NPC260233
0.6543	Remote Similarity	NPC198841
0.6543	Remote Similarity	NPC269586
0.6538	Remote Similarity	NPC49994
0.6535	Remote Similarity	NPC153885
0.6535	Remote Similarity	NPC59677
0.6526	Remote Similarity	NPC14326
0.6526	Remote Similarity	NPC230068
0.6514	Remote Similarity	NPC21929
0.6514	Remote Similarity	NPC27252
0.6514	Remote Similarity	NPC472979
0.6481	Remote Similarity	NPC474559
0.6477	Remote Similarity	NPC473206
0.6471	Remote Similarity	NPC238219
0.6471	Remote Similarity	NPC469330
0.6471	Remote Similarity	NPC289883
0.6471	Remote Similarity	NPC50266
0.6471	Remote Similarity	NPC322040
0.6455	Remote Similarity	NPC149455
0.6455	Remote Similarity	NPC470252
0.6455	Remote Similarity	NPC472982
0.6455	Remote Similarity	NPC64642
0.6455	Remote Similarity	NPC475006
0.6452	Remote Similarity	NPC103488
0.6444	Remote Similarity	NPC212463
0.6436	Remote Similarity	NPC475023
0.6436	Remote Similarity	NPC133461
0.6436	Remote Similarity	NPC475059
0.642	Remote Similarity	NPC149436
0.642	Remote Similarity	NPC277704
0.64	Remote Similarity	NPC176858
0.6374	Remote Similarity	NPC299134
0.6373	Remote Similarity	NPC475057
0.6373	Remote Similarity	NPC155232
0.6373	Remote Similarity	NPC108800
0.6364	Remote Similarity	NPC472980
0.6364	Remote Similarity	NPC473031
0.6353	Remote Similarity	NPC200745
0.6346	Remote Similarity	NPC471320
0.6346	Remote Similarity	NPC471319
0.6339	Remote Similarity	NPC95126
0.6339	Remote Similarity	NPC475002
0.6339	Remote Similarity	NPC265513
0.6337	Remote Similarity	NPC277277
0.6337	Remote Similarity	NPC191444
0.6316	Remote Similarity	NPC285716
0.6316	Remote Similarity	NPC157055
0.6316	Remote Similarity	NPC17408
0.6311	Remote Similarity	NPC119326
0.631	Remote Similarity	NPC169110
0.63	Remote Similarity	NPC267262
0.63	Remote Similarity	NPC111233
0.63	Remote Similarity	NPC12429
0.6296	Remote Similarity	NPC472691
0.6296	Remote Similarity	NPC474866
0.6296	Remote Similarity	NPC471829
0.6296	Remote Similarity	NPC475939
0.6292	Remote Similarity	NPC297358
0.6289	Remote Similarity	NPC474088
0.6283	Remote Similarity	NPC471189
0.6283	Remote Similarity	NPC280789
0.6283	Remote Similarity	NPC471188
0.6263	Remote Similarity	NPC160339
0.6263	Remote Similarity	NPC307
0.6262	Remote Similarity	NPC245927
0.625	Remote Similarity	NPC478140
0.625	Remote Similarity	NPC108339
0.625	Remote Similarity	NPC109151
0.625	Remote Similarity	NPC472880
0.624	Remote Similarity	NPC126458
0.6238	Remote Similarity	NPC470877
0.6228	Remote Similarity	NPC93287
0.6214	Remote Similarity	NPC314690
0.6214	Remote Similarity	NPC188844
0.6214	Remote Similarity	NPC1682
0.618	Remote Similarity	NPC22760
0.6176	Remote Similarity	NPC19256
0.6176	Remote Similarity	NPC471307

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC60408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	1011
0.2-0.3	1341
0.3-0.4	3457
0.4-0.5	2147
0.5-0.6	682
0.6-0.7	181
0.7-0.8	67
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8876	High Similarity	NPD3980	Approved
0.8876	High Similarity	NPD2878	Approved
0.8876	High Similarity	NPD3982	Approved
0.8488	Intermediate Similarity	NPD4544	Approved
0.8202	Intermediate Similarity	NPD3426	Approved
0.8202	Intermediate Similarity	NPD3428	Approved
0.8191	Intermediate Similarity	NPD5598	Approved
0.8191	Intermediate Similarity	NPD5597	Approved
0.8161	Intermediate Similarity	NPD2001	Discontinued
0.8023	Intermediate Similarity	NPD260	Discontinued
0.7955	Intermediate Similarity	NPD4635	Approved
0.7935	Intermediate Similarity	NPD5915	Approved
0.7889	Intermediate Similarity	NPD3099	Discontinued
0.7865	Intermediate Similarity	NPD3427	Approved
0.7865	Intermediate Similarity	NPD3429	Approved
0.7816	Intermediate Similarity	NPD1617	Discontinued
0.7802	Intermediate Similarity	NPD4146	Approved
0.7802	Intermediate Similarity	NPD2002	Discontinued
0.7802	Intermediate Similarity	NPD4145	Approved
0.7766	Intermediate Similarity	NPD4408	Approved
0.7766	Intermediate Similarity	NPD4407	Approved
0.7766	Intermediate Similarity	NPD4405	Approved
0.7727	Intermediate Similarity	NPD3035	Approved
0.7692	Intermediate Similarity	NPD4636	Approved
0.7692	Intermediate Similarity	NPD4409	Approved
0.7692	Intermediate Similarity	NPD4406	Approved
0.766	Intermediate Similarity	NPD4543	Discontinued
0.764	Intermediate Similarity	NPD4170	Approved
0.764	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4169	Approved
0.7634	Intermediate Similarity	NPD771	Phase 3
0.7614	Intermediate Similarity	NPD3979	Approved
0.7614	Intermediate Similarity	NPD3904	Approved
0.7614	Intermediate Similarity	NPD3981	Approved
0.7614	Intermediate Similarity	NPD3903	Approved
0.7604	Intermediate Similarity	NPD5554	Approved
0.7586	Intermediate Similarity	NPD9564	Approved
0.7586	Intermediate Similarity	NPD79	Approved
0.7586	Intermediate Similarity	NPD9563	Approved
0.7553	Intermediate Similarity	NPD3344	Approved
0.7553	Intermediate Similarity	NPD3346	Approved
0.7551	Intermediate Similarity	NPD5832	Phase 3
0.7529	Intermediate Similarity	NPD9593	Approved
0.7529	Intermediate Similarity	NPD9594	Approved
0.7529	Intermediate Similarity	NPD9588	Approved
0.7529	Intermediate Similarity	NPD9592	Approved
0.7529	Intermediate Similarity	NPD80	Approved
0.7529	Intermediate Similarity	NPD9591	Approved
0.7529	Intermediate Similarity	NPD9590	Approved
0.7529	Intermediate Similarity	NPD9589	Approved
0.7528	Intermediate Similarity	NPD4026	Approved
0.7528	Intermediate Similarity	NPD4027	Approved
0.7527	Intermediate Similarity	NPD5675	Discontinued
0.7527	Intermediate Similarity	NPD3345	Approved
0.7526	Intermediate Similarity	NPD2895	Discontinued
0.7526	Intermediate Similarity	NPD2005	Discontinued
0.7525	Intermediate Similarity	NPD4936	Approved
0.7525	Intermediate Similarity	NPD4937	Approved
0.75	Intermediate Similarity	NPD4545	Approved
0.75	Intermediate Similarity	NPD4542	Approved
0.7471	Intermediate Similarity	NPD4147	Approved
0.7471	Intermediate Similarity	NPD4144	Approved
0.7449	Intermediate Similarity	NPD713	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2208	Approved
0.7391	Intermediate Similarity	NPD2205	Approved
0.7391	Intermediate Similarity	NPD5916	Discontinued
0.7347	Intermediate Similarity	NPD6472	Discontinued
0.7326	Intermediate Similarity	NPD505	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD590	Approved
0.7303	Intermediate Similarity	NPD589	Approved
0.73	Intermediate Similarity	NPD4737	Phase 2
0.7294	Intermediate Similarity	NPD292	Approved
0.7294	Intermediate Similarity	NPD294	Approved
0.7234	Intermediate Similarity	NPD781	Approved
0.7234	Intermediate Similarity	NPD782	Approved
0.7234	Intermediate Similarity	NPD783	Approved
0.7234	Intermediate Similarity	NPD780	Approved
0.7212	Intermediate Similarity	NPD7170	Discontinued
0.7191	Intermediate Similarity	NPD295	Approved
0.7191	Intermediate Similarity	NPD293	Approved
0.7191	Intermediate Similarity	NPD296	Approved
0.7172	Intermediate Similarity	NPD5963	Phase 2
0.7172	Intermediate Similarity	NPD5964	Phase 2
0.7143	Intermediate Similarity	NPD2207	Approved
0.7143	Intermediate Similarity	NPD2206	Approved
0.7129	Intermediate Similarity	NPD1946	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5178	Approved
0.7083	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1916	Discontinued
0.703	Intermediate Similarity	NPD4117	Approved
0.703	Intermediate Similarity	NPD4813	Approved
0.703	Intermediate Similarity	NPD4263	Approved
0.7021	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9393	Approved
0.7	Intermediate Similarity	NPD9397	Approved
0.7	Intermediate Similarity	NPD1738	Approved
0.699	Remote Similarity	NPD5753	Discontinued
0.6989	Remote Similarity	NPD831	Approved
0.6989	Remote Similarity	NPD830	Approved
0.6947	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3495	Discontinued
0.6915	Remote Similarity	NPD2538	Approved
0.6915	Remote Similarity	NPD2539	Approved
0.6915	Remote Similarity	NPD785	Approved
0.6903	Remote Similarity	NPD5511	Discontinued
0.69	Remote Similarity	NPD4094	Approved
0.69	Remote Similarity	NPD6049	Phase 2
0.69	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5630	Phase 1
0.6867	Remote Similarity	NPD675	Discontinued
0.6857	Remote Similarity	NPD1026	Approved
0.6857	Remote Similarity	NPD2980	Phase 2
0.6857	Remote Similarity	NPD1028	Approved
0.6848	Remote Similarity	NPD5371	Approved
0.6848	Remote Similarity	NPD5372	Approved
0.6827	Remote Similarity	NPD5716	Approved
0.6827	Remote Similarity	NPD4119	Approved
0.6818	Remote Similarity	NPD9728	Phase 1
0.6809	Remote Similarity	NPD4000	Phase 3
0.6783	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3000	Approved
0.6768	Remote Similarity	NPD2998	Approved
0.6768	Remote Similarity	NPD2997	Approved
0.6765	Remote Similarity	NPD4657	Approved
0.6765	Remote Similarity	NPD4655	Approved
0.6739	Remote Similarity	NPD1051	Approved
0.6739	Remote Similarity	NPD1053	Approved
0.6739	Remote Similarity	NPD1052	Approved
0.6737	Remote Similarity	NPD9395	Approved
0.6733	Remote Similarity	NPD2656	Approved
0.6733	Remote Similarity	NPD2655	Approved
0.6731	Remote Similarity	NPD6354	Discontinued
0.6727	Remote Similarity	NPD1935	Phase 3
0.6703	Remote Similarity	NPD603	Approved
0.6667	Remote Similarity	NPD6024	Approved
0.6667	Remote Similarity	NPD2841	Approved
0.6667	Remote Similarity	NPD6027	Approved
0.6667	Remote Similarity	NPD3093	Approved
0.6636	Remote Similarity	NPD1269	Approved
0.6636	Remote Similarity	NPD5717	Approved
0.6636	Remote Similarity	NPD1268	Approved
0.6635	Remote Similarity	NPD4007	Approved
0.6635	Remote Similarity	NPD4008	Approved
0.6635	Remote Similarity	NPD524	Approved
0.6635	Remote Similarity	NPD523	Approved
0.6634	Remote Similarity	NPD6548	Approved
0.6634	Remote Similarity	NPD6549	Approved
0.6609	Remote Similarity	NPD2396	Approved
0.6609	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2395	Approved
0.66	Remote Similarity	NPD517	Discontinued
0.66	Remote Similarity	NPD7160	Approved
0.6588	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2039	Approved
0.6577	Remote Similarity	NPD2038	Approved
0.6569	Remote Similarity	NPD3772	Phase 3
0.6549	Remote Similarity	NPD2508	Discontinued
0.6509	Remote Similarity	NPD4734	Approved
0.6509	Remote Similarity	NPD4719	Phase 2
0.6509	Remote Similarity	NPD4735	Approved
0.6505	Remote Similarity	NPD3456	Approved
0.6505	Remote Similarity	NPD3457	Approved
0.6505	Remote Similarity	NPD3458	Approved
0.6491	Remote Similarity	NPD4031	Approved
0.6491	Remote Similarity	NPD4032	Approved
0.6481	Remote Similarity	NPD1765	Approved
0.6481	Remote Similarity	NPD1767	Approved
0.6481	Remote Similarity	NPD1763	Approved
0.6481	Remote Similarity	NPD1766	Approved
0.6481	Remote Similarity	NPD1761	Approved
0.6471	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD736	Approved
0.6471	Remote Similarity	NPD3719	Approved
0.6471	Remote Similarity	NPD3718	Approved
0.6471	Remote Similarity	NPD8	Approved
0.6471	Remote Similarity	NPD243	Approved
0.6471	Remote Similarity	NPD735	Approved
0.646	Remote Similarity	NPD7060	Approved
0.646	Remote Similarity	NPD7059	Approved
0.6458	Remote Similarity	NPD262	Approved
0.6458	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD263	Approved
0.6458	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8009	Approved
0.6455	Remote Similarity	NPD8010	Approved
0.6449	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5838	Phase 2
0.6429	Remote Similarity	NPD304	Approved
0.6429	Remote Similarity	NPD305	Approved
0.6421	Remote Similarity	NPD472	Approved
0.641	Remote Similarity	NPD5516	Phase 2
0.641	Remote Similarity	NPD5517	Phase 2
0.641	Remote Similarity	NPD1710	Approved
0.6408	Remote Similarity	NPD4814	Discontinued
0.6404	Remote Similarity	NPD4674	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD507	Approved
0.6383	Remote Similarity	NPD508	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data