NPASS Compound

Structure

CID899 OpenBabel06191715322D 23 25 0 0 1 0 0 0 0 0999 V2000 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 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 4.3301 0.5000 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 3.4641 -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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 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 23 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 6 0 0 0 18 20 1 6 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 3 1 6 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	355.774
LogP:	4.556
LogD:	4.19
LogS:	-4.88
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.647
Synthetic Accessibility Score:	4.166
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	2.758026857918594e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.884
30% Bioavailability (F30%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	97.70359802246094%
Volume Distribution (VD):	1.011
Pgp-substrate:	1.7346200942993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.386
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.638
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.638
CYP2C9-substrate:	0.385
CYP2D6-inhibitor:	0.379
CYP2D6-substrate:	0.53
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.718

ADMET: Excretion

Clearance (CL):	2.515
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.948
Carcinogencity:	0.066
Eye Corrosion:	0.421
Eye Irritation:	0.9
Respiratory Toxicity:	0.844

Download Data

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

Natural Product: NPC899

Natural Product ID:	NPC899
*Common Name:**	Methyl Abietate
IUPAC Name:	methyl (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate
Synonyms:	Methyl Abietadien-18-oate; Methyl Abietate
Standard InCHIKey:	OVXRPXGVKBHGQO-UYWIDEMCSA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-14(2)15-7-9-17-16(13-15)8-10-18-20(17,3)11-6-12-21(18,4)19(22)23-5/h8,13-14,17-18H,6-7,9-12H2,1-5H3/t17-,18+,20+,21+/m0/s1
SMILES:	CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(=O)OC)[C@H]2CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509586
PubChem CID:	173058
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
NPO25880	Sarcococca coriacea	Species	Buxaceae	Eukaryota	leaves	Nepalese	n.a.	PMID[11421762]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[16644542]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[16644542]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO24299	Litsea laurifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24299	Litsea laurifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10310	Cutaneotrichosporon cutaneum	Species	Trichosporonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24299	Litsea laurifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20800	Pholiota nameko	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6478	Tubifera ferruginosa	Species	Reticulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24479	Phaseolus atropurpureus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593.1	Pinus sylvestris var. hamata	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25483	Croton cortesianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24568	Spongia zimocca	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26279	Premna schimperi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9829	Arnica chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26582	Erigeron sumatrensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26464	Macaranga indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26799	Vitis heyneana	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25880	Sarcococca coriacea	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25421	Stemodia viscosa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6851	Aplysilla pallida	Species	Darwinellidae	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
IC50	3
MIC	4
Others	7
Potency	26

Activity Type	# Activity
Cell Line	7
Individual Protein	3
Organism	6
Others	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	3.6	ug.mL-1	PMID[495481]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	49.4	ug.mL-1	PMID[495481]
NPT165	Cell Line	HeLa	Homo sapiens	CC100	=	50.0	ug ml-1	PMID[495481]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	11000.0	nM	PMID[495482]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	81310.0	nM	PMID[495483]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	79320.0	nM	PMID[495483]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	63100.0	nM	PMID[495483]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	48972.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Selectivity Index	=	13.7	n.a.	PMID[495481]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	10.0	n.a.	PMID[495481]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	6.25	ug ml-1	PMID[495481]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[495484]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	75.0	ug.mL-1	PMID[495484]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	75.0	ug.mL-1	PMID[495484]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	=	50.0	ug.mL-1	PMID[495484]
NPT2	Others	Unspecified		Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3890	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1737.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48972.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	544.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	243.4	nM	PubChem BioAssay data set

☑ 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 NPC899 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	193
0.1-0.2	1122
0.2-0.3	5660
0.3-0.4	16760
0.4-0.5	8791
0.5-0.6	6446
0.6-0.7	2975
0.7-0.8	695
0.8-0.85	44
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC4827
0.9714	High Similarity	NPC306928
0.9178	High Similarity	NPC309399
0.9167	High Similarity	NPC166797
0.8904	High Similarity	NPC301065
0.8831	High Similarity	NPC474955
0.88	High Similarity	NPC472300
0.8701	High Similarity	NPC104545
0.8701	High Similarity	NPC267517
0.8684	High Similarity	NPC321514
0.863	High Similarity	NPC160817
0.8608	High Similarity	NPC83569
0.8608	High Similarity	NPC69279
0.859	High Similarity	NPC142244
0.8571	High Similarity	NPC327674
0.8553	High Similarity	NPC471897
0.8553	High Similarity	NPC471899
0.8553	High Similarity	NPC107039
0.8537	High Similarity	NPC24816
0.8533	High Similarity	NPC476844
0.8533	High Similarity	NPC279666
0.8533	High Similarity	NPC192540
0.8481	Intermediate Similarity	NPC296367
0.8481	Intermediate Similarity	NPC15910
0.8462	Intermediate Similarity	NPC477057
0.8442	Intermediate Similarity	NPC280654
0.8442	Intermediate Similarity	NPC260385
0.8442	Intermediate Similarity	NPC110094
0.8421	Intermediate Similarity	NPC69143
0.8421	Intermediate Similarity	NPC89294
0.84	Intermediate Similarity	NPC476046
0.84	Intermediate Similarity	NPC161923
0.84	Intermediate Similarity	NPC237591
0.84	Intermediate Similarity	NPC103958
0.84	Intermediate Similarity	NPC251970
0.84	Intermediate Similarity	NPC183503
0.84	Intermediate Similarity	NPC3753
0.84	Intermediate Similarity	NPC283908
0.84	Intermediate Similarity	NPC241854
0.8395	Intermediate Similarity	NPC76333
0.8395	Intermediate Similarity	NPC2709
0.8375	Intermediate Similarity	NPC70834
0.8375	Intermediate Similarity	NPC200752
0.8354	Intermediate Similarity	NPC38350
0.8354	Intermediate Similarity	NPC201912
0.8354	Intermediate Similarity	NPC327002
0.8333	Intermediate Similarity	NPC196827
0.8333	Intermediate Similarity	NPC274996
0.8333	Intermediate Similarity	NPC231431
0.8333	Intermediate Similarity	NPC16394
0.8333	Intermediate Similarity	NPC199595
0.8313	Intermediate Similarity	NPC472220
0.8313	Intermediate Similarity	NPC97884
0.8272	Intermediate Similarity	NPC312660
0.8267	Intermediate Similarity	NPC279241
0.825	Intermediate Similarity	NPC240302
0.825	Intermediate Similarity	NPC327969
0.825	Intermediate Similarity	NPC321289
0.825	Intermediate Similarity	NPC260956
0.8228	Intermediate Similarity	NPC37038
0.8214	Intermediate Similarity	NPC84271
0.8214	Intermediate Similarity	NPC102414
0.8214	Intermediate Similarity	NPC77168
0.8214	Intermediate Similarity	NPC475049
0.8205	Intermediate Similarity	NPC179028
0.8193	Intermediate Similarity	NPC477228
0.8182	Intermediate Similarity	NPC41017
0.8171	Intermediate Similarity	NPC470048
0.8171	Intermediate Similarity	NPC470223
0.814	Intermediate Similarity	NPC263780
0.8125	Intermediate Similarity	NPC221647
0.8125	Intermediate Similarity	NPC471898
0.8125	Intermediate Similarity	NPC278459
0.8125	Intermediate Similarity	NPC147066
0.8125	Intermediate Similarity	NPC263272
0.8125	Intermediate Similarity	NPC267691
0.8125	Intermediate Similarity	NPC274050
0.8125	Intermediate Similarity	NPC162632
0.8101	Intermediate Similarity	NPC477371
0.8101	Intermediate Similarity	NPC28319
0.8095	Intermediate Similarity	NPC472302
0.8082	Intermediate Similarity	NPC193770
0.8077	Intermediate Similarity	NPC165711
0.8072	Intermediate Similarity	NPC329943
0.8072	Intermediate Similarity	NPC10005
0.8072	Intermediate Similarity	NPC324063
0.8072	Intermediate Similarity	NPC73038
0.8072	Intermediate Similarity	NPC325594
0.8072	Intermediate Similarity	NPC195640
0.8072	Intermediate Similarity	NPC9892
0.8072	Intermediate Similarity	NPC264127
0.8072	Intermediate Similarity	NPC91525
0.8052	Intermediate Similarity	NPC476795
0.8049	Intermediate Similarity	NPC320801
0.8049	Intermediate Similarity	NPC100391
0.8049	Intermediate Similarity	NPC156981
0.8025	Intermediate Similarity	NPC69101
0.8025	Intermediate Similarity	NPC251779
0.8025	Intermediate Similarity	NPC100297
0.8025	Intermediate Similarity	NPC73882
0.8025	Intermediate Similarity	NPC142683
0.8023	Intermediate Similarity	NPC301244
0.8023	Intermediate Similarity	NPC470036
0.8023	Intermediate Similarity	NPC174167
0.8	Intermediate Similarity	NPC195424
0.8	Intermediate Similarity	NPC284561
0.8	Intermediate Similarity	NPC474972
0.8	Intermediate Similarity	NPC161751
0.8	Intermediate Similarity	NPC95246
0.7976	Intermediate Similarity	NPC233836
0.7976	Intermediate Similarity	NPC46912
0.7976	Intermediate Similarity	NPC159046
0.7976	Intermediate Similarity	NPC71507
0.7976	Intermediate Similarity	NPC162107
0.7976	Intermediate Similarity	NPC181327
0.7976	Intermediate Similarity	NPC187376
0.7975	Intermediate Similarity	NPC35574
0.7975	Intermediate Similarity	NPC469996
0.7975	Intermediate Similarity	NPC189485
0.7975	Intermediate Similarity	NPC74410
0.7975	Intermediate Similarity	NPC239098
0.7952	Intermediate Similarity	NPC474537
0.7952	Intermediate Similarity	NPC323765
0.7949	Intermediate Similarity	NPC180886
0.7931	Intermediate Similarity	NPC152897
0.7931	Intermediate Similarity	NPC66429
0.7927	Intermediate Similarity	NPC102197
0.7927	Intermediate Similarity	NPC271784
0.7927	Intermediate Similarity	NPC310470
0.7922	Intermediate Similarity	NPC213223
0.7907	Intermediate Similarity	NPC175628
0.7907	Intermediate Similarity	NPC148414
0.7907	Intermediate Similarity	NPC469595
0.7907	Intermediate Similarity	NPC212679
0.7907	Intermediate Similarity	NPC220454
0.7907	Intermediate Similarity	NPC111585
0.7901	Intermediate Similarity	NPC40228
0.7901	Intermediate Similarity	NPC229584
0.7901	Intermediate Similarity	NPC473420
0.7901	Intermediate Similarity	NPC474085
0.7901	Intermediate Similarity	NPC14203
0.7901	Intermediate Similarity	NPC476988
0.7901	Intermediate Similarity	NPC477372
0.7901	Intermediate Similarity	NPC121984
0.7882	Intermediate Similarity	NPC474845
0.7882	Intermediate Similarity	NPC40552
0.7882	Intermediate Similarity	NPC72397
0.7882	Intermediate Similarity	NPC28227
0.7882	Intermediate Similarity	NPC246708
0.7882	Intermediate Similarity	NPC224145
0.7875	Intermediate Similarity	NPC158565
0.7875	Intermediate Similarity	NPC158846
0.7875	Intermediate Similarity	NPC474113
0.7857	Intermediate Similarity	NPC55309
0.7857	Intermediate Similarity	NPC155011
0.7857	Intermediate Similarity	NPC262085
0.7857	Intermediate Similarity	NPC322159
0.7857	Intermediate Similarity	NPC28252
0.7841	Intermediate Similarity	NPC56525
0.7841	Intermediate Similarity	NPC80365
0.7841	Intermediate Similarity	NPC469406
0.7831	Intermediate Similarity	NPC139566
0.7831	Intermediate Similarity	NPC109512
0.7831	Intermediate Similarity	NPC165064
0.7831	Intermediate Similarity	NPC96095
0.7831	Intermediate Similarity	NPC477289
0.7821	Intermediate Similarity	NPC201027
0.7821	Intermediate Similarity	NPC65650
0.7821	Intermediate Similarity	NPC228978
0.7816	Intermediate Similarity	NPC204341
0.7816	Intermediate Similarity	NPC26888
0.7816	Intermediate Similarity	NPC297265
0.7805	Intermediate Similarity	NPC133391
0.7805	Intermediate Similarity	NPC320514
0.7805	Intermediate Similarity	NPC163236
0.7792	Intermediate Similarity	NPC35656
0.7792	Intermediate Similarity	NPC36310
0.7791	Intermediate Similarity	NPC474570
0.7791	Intermediate Similarity	NPC474700
0.7791	Intermediate Similarity	NPC36668
0.7791	Intermediate Similarity	NPC469546
0.7791	Intermediate Similarity	NPC118011
0.7791	Intermediate Similarity	NPC173042
0.7791	Intermediate Similarity	NPC112454
0.7791	Intermediate Similarity	NPC470588
0.7791	Intermediate Similarity	NPC474686
0.7791	Intermediate Similarity	NPC474889
0.7778	Intermediate Similarity	NPC2482
0.7778	Intermediate Similarity	NPC474956
0.7778	Intermediate Similarity	NPC474978
0.7778	Intermediate Similarity	NPC26139
0.7778	Intermediate Similarity	NPC269791
0.7765	Intermediate Similarity	NPC51700
0.7765	Intermediate Similarity	NPC158141
0.7765	Intermediate Similarity	NPC173089
0.7765	Intermediate Similarity	NPC18064
0.7765	Intermediate Similarity	NPC242468
0.7765	Intermediate Similarity	NPC96496
0.7765	Intermediate Similarity	NPC98442
0.7765	Intermediate Similarity	NPC102683

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 NPC899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1417
0.2-0.3	4071
0.3-0.4	2366
0.4-0.5	651
0.5-0.6	317
0.6-0.7	109
0.7-0.8	38
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD5330	Approved
0.8072	Intermediate Similarity	NPD7334	Approved
0.8072	Intermediate Similarity	NPD7146	Approved
0.8072	Intermediate Similarity	NPD7521	Approved
0.8072	Intermediate Similarity	NPD6409	Approved
0.8072	Intermediate Similarity	NPD6684	Approved
0.8023	Intermediate Similarity	NPD6050	Approved
0.7907	Intermediate Similarity	NPD5207	Approved
0.7907	Intermediate Similarity	NPD5692	Phase 3
0.7882	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6672	Approved
0.7882	Intermediate Similarity	NPD6903	Approved
0.7882	Intermediate Similarity	NPD5737	Approved
0.7857	Intermediate Similarity	NPD6098	Approved
0.7821	Intermediate Similarity	NPD8039	Approved
0.7816	Intermediate Similarity	NPD5694	Approved
0.7791	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5733	Approved
0.7614	Intermediate Similarity	NPD5284	Approved
0.7614	Intermediate Similarity	NPD6411	Approved
0.7614	Intermediate Similarity	NPD5281	Approved
0.759	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6673	Approved
0.7586	Intermediate Similarity	NPD6080	Approved
0.7586	Intermediate Similarity	NPD6904	Approved
0.7558	Intermediate Similarity	NPD3573	Approved
0.7528	Intermediate Similarity	NPD6399	Phase 3
0.7471	Intermediate Similarity	NPD5208	Approved
0.7468	Intermediate Similarity	NPD4687	Approved
0.7444	Intermediate Similarity	NPD7900	Approved
0.7444	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7748	Approved
0.7442	Intermediate Similarity	NPD5280	Approved
0.7442	Intermediate Similarity	NPD5279	Phase 3
0.7442	Intermediate Similarity	NPD4694	Approved
0.7436	Intermediate Similarity	NPD5276	Approved
0.7416	Intermediate Similarity	NPD7515	Phase 2
0.7412	Intermediate Similarity	NPD4786	Approved
0.7386	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6101	Approved
0.7381	Intermediate Similarity	NPD3667	Approved
0.7363	Intermediate Similarity	NPD5695	Phase 3
0.7363	Intermediate Similarity	NPD5654	Approved
0.7363	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7732	Phase 3
0.725	Intermediate Similarity	NPD4058	Approved
0.7234	Intermediate Similarity	NPD6404	Discontinued
0.7222	Intermediate Similarity	NPD5693	Phase 1
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7209	Intermediate Similarity	NPD3133	Approved
0.7209	Intermediate Similarity	NPD3666	Approved
0.7209	Intermediate Similarity	NPD3665	Phase 1
0.7204	Intermediate Similarity	NPD6084	Phase 2
0.7204	Intermediate Similarity	NPD5959	Approved
0.7204	Intermediate Similarity	NPD7902	Approved
0.7204	Intermediate Similarity	NPD6083	Phase 2
0.7179	Intermediate Similarity	NPD4137	Phase 3
0.7176	Intermediate Similarity	NPD4221	Approved
0.7176	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7126	Intermediate Similarity	NPD5329	Approved
0.7089	Intermediate Similarity	NPD4691	Approved
0.7089	Intermediate Similarity	NPD4747	Approved
0.7065	Intermediate Similarity	NPD6001	Approved
0.7051	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3618	Phase 1
0.7045	Intermediate Similarity	NPD5690	Phase 2
0.7011	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD5328	Approved
0.6957	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD5778	Approved
0.6947	Remote Similarity	NPD5696	Approved
0.6932	Remote Similarity	NPD1694	Approved
0.6932	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4096	Approved
0.6915	Remote Similarity	NPD7614	Phase 1
0.6905	Remote Similarity	NPD3617	Approved
0.686	Remote Similarity	NPD4692	Approved
0.686	Remote Similarity	NPD4139	Approved
0.6854	Remote Similarity	NPD4519	Discontinued
0.6854	Remote Similarity	NPD4688	Approved
0.6854	Remote Similarity	NPD4693	Phase 3
0.6854	Remote Similarity	NPD4689	Approved
0.6854	Remote Similarity	NPD5205	Approved
0.6854	Remote Similarity	NPD4623	Approved
0.6854	Remote Similarity	NPD4138	Approved
0.6854	Remote Similarity	NPD4690	Approved
0.6848	Remote Similarity	NPD6079	Approved
0.6813	Remote Similarity	NPD4753	Phase 2
0.6813	Remote Similarity	NPD6051	Approved
0.6774	Remote Similarity	NPD5133	Approved
0.6753	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4518	Approved
0.67	Remote Similarity	NPD6402	Approved
0.67	Remote Similarity	NPD5739	Approved
0.67	Remote Similarity	NPD7128	Approved
0.67	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7645	Phase 2
0.6598	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD4202	Approved
0.6585	Remote Similarity	NPD5777	Approved
0.6585	Remote Similarity	NPD4243	Approved
0.6571	Remote Similarity	NPD6858	Approved
0.6571	Remote Similarity	NPD7094	Approved
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD7320	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6562	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6942	Approved
0.6548	Remote Similarity	NPD7339	Approved
0.6535	Remote Similarity	NPD6008	Approved
0.6531	Remote Similarity	NPD7640	Approved
0.6531	Remote Similarity	NPD7639	Approved
0.6517	Remote Similarity	NPD4788	Approved
0.6505	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD6373	Approved
0.6479	Remote Similarity	NPD28	Approved
0.6479	Remote Similarity	NPD29	Approved
0.6477	Remote Similarity	NPD8028	Phase 2
0.6471	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD6614	Approved
0.6471	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5697	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6458	Remote Similarity	NPD4629	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6437	Remote Similarity	NPD4195	Approved
0.6429	Remote Similarity	NPD6924	Approved
0.6429	Remote Similarity	NPD4785	Approved
0.6429	Remote Similarity	NPD4784	Approved
0.6429	Remote Similarity	NPD6926	Approved
0.6408	Remote Similarity	NPD6011	Approved
0.6392	Remote Similarity	NPD4697	Phase 3
0.6392	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5222	Approved
0.6392	Remote Similarity	NPD5221	Approved
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD6649	Approved
0.6381	Remote Similarity	NPD6869	Approved
0.6375	Remote Similarity	NPD4224	Phase 2
0.6375	Remote Similarity	NPD7331	Phase 2
0.6364	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD8264	Approved
0.6346	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD6014	Approved
0.6346	Remote Similarity	NPD6012	Approved
0.6327	Remote Similarity	NPD5173	Approved
0.6327	Remote Similarity	NPD4755	Approved
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6882	Approved
0.6321	Remote Similarity	NPD8297	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6316	Remote Similarity	NPD287	Approved
0.6311	Remote Similarity	NPD6412	Phase 2
0.6282	Remote Similarity	NPD4194	Approved
0.6282	Remote Similarity	NPD4193	Approved
0.6282	Remote Similarity	NPD4192	Approved
0.6282	Remote Similarity	NPD4191	Approved
0.6279	Remote Similarity	NPD6933	Approved
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.6235	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3194	Approved
0.6216	Remote Similarity	NPD3195	Phase 2
0.6216	Remote Similarity	NPD3196	Approved
0.6216	Remote Similarity	NPD4266	Approved
0.6211	Remote Similarity	NPD3672	Approved
0.6211	Remote Similarity	NPD3673	Approved
0.62	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD4696	Approved
0.62	Remote Similarity	NPD5286	Approved
0.62	Remote Similarity	NPD4700	Approved
0.619	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6081	Approved
0.6186	Remote Similarity	NPD5707	Approved
0.618	Remote Similarity	NPD7525	Registered
0.6163	Remote Similarity	NPD4190	Phase 3
0.6163	Remote Similarity	NPD5275	Approved
0.6163	Remote Similarity	NPD3702	Approved
0.6154	Remote Similarity	NPD5362	Discontinued
0.6147	Remote Similarity	NPD6868	Approved
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6139	Remote Similarity	NPD5223	Approved
0.6129	Remote Similarity	NPD6422	Discontinued
0.6111	Remote Similarity	NPD857	Phase 3
0.6111	Remote Similarity	NPD4632	Approved
0.6111	Remote Similarity	NPD5369	Approved
0.6092	Remote Similarity	NPD6117	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