NPASS Compound

Structure

CID35797 OpenBabel06191715362D 22 24 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 1.3660 2.3660 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 0.0000 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 -0.8660 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 0.8660 -0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 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 -1.7321 -0.0000 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 -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 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.39
LogD:	3.929
LogS:	-3.907
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.843
Synthetic Accessibility Score:	3.713
Fsp3:	0.7
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:	-4.684
MDCK Permeability:	2.0107388991164044e-05
Pgp-inhibitor:	0.321
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	97.20032501220703%
Volume Distribution (VD):	2.261
Pgp-substrate:	3.1504273414611816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.47
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.517
CYP2D6-inhibitor:	0.757
CYP2D6-substrate:	0.447
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.649

ADMET: Excretion

Clearance (CL):	14.725
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.844
Carcinogencity:	0.118
Eye Corrosion:	0.004
Eye Irritation:	0.26
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC35797

Natural Product ID:	NPC35797
*Common Name:**	(4Bs,8S,8Ar)-8-(Hydroxymethyl)-4B,8-Dimethyl-2-Propan-2-Yl-5,6,7,8A,9,10-Hexahydrophenanthren-3-Ol
IUPAC Name:	(4bS,8S,8aR)-8-(hydroxymethyl)-4b,8-dimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
Synonyms:
Standard InCHIKey:	ZSMYLYMVTJVQIR-XUVXKRRUSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)15-10-14-6-7-18-19(3,12-21)8-5-9-20(18,4)16(14)11-17(15)22/h10-11,13,18,21-22H,5-9,12H2,1-4H3/t18-,19+,20+/m0/s1
SMILES:	OC[C@@]1(C)CCC[C@]2([C@H]1CCc1c2cc(c(c1)C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3343893
PubChem CID:	21632843
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
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7646	Edgeworthia chrysantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8215	Crepis zacintha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	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
GI50	3
IC50	4
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	2
Organism	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14000.0	nM	PMID[572641]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	92000.0	nM	PMID[572642]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[572642]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Inhibition	=	20.0	%	PMID[572642]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	51000.0	nM	PMID[572642]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	91000.0	nM	PMID[572642]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	=	14000.0	nM	PMID[572640]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	14000.0	nM	PMID[572640]
NPT21657	SINGLE PROTEIN	DNA topoisomerase I	Bos taurus	Inhibition	=	30.0	%	PMID[572642]

☑ 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 NPC35797 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	275
0.1-0.2	1530
0.2-0.3	3198
0.3-0.4	9398
0.4-0.5	10163
0.5-0.6	10030
0.6-0.7	6363
0.7-0.8	1453
0.8-0.85	166
0.85-0.9	78
0.9-0.95	21
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192948
0.9907	High Similarity	NPC477137
0.9907	High Similarity	NPC38893
0.9907	High Similarity	NPC308311
0.9817	High Similarity	NPC304510
0.9817	High Similarity	NPC172219
0.9727	High Similarity	NPC471671
0.9725	High Similarity	NPC219112
0.9722	High Similarity	NPC268160
0.964	High Similarity	NPC469644
0.9636	High Similarity	NPC477136
0.9633	High Similarity	NPC147179
0.9626	High Similarity	NPC260323
0.9626	High Similarity	NPC176279
0.9545	High Similarity	NPC469663
0.9545	High Similarity	NPC308828
0.9545	High Similarity	NPC92
0.9375	High Similarity	NPC469609
0.9375	High Similarity	NPC154030
0.9369	High Similarity	NPC471668
0.9364	High Similarity	NPC195922
0.9358	High Similarity	NPC250323
0.9352	High Similarity	NPC132720
0.9352	High Similarity	NPC141782
0.9252	High Similarity	NPC151477
0.9224	High Similarity	NPC471187
0.9182	High Similarity	NPC228425
0.9182	High Similarity	NPC46940
0.9174	High Similarity	NPC13482
0.9145	High Similarity	NPC181334
0.9138	High Similarity	NPC11250
0.9123	High Similarity	NPC93071
0.9123	High Similarity	NPC126002
0.9099	High Similarity	NPC715
0.9091	High Similarity	NPC95716
0.9065	High Similarity	NPC117115
0.9043	High Similarity	NPC135467
0.9043	High Similarity	NPC260832
0.9035	High Similarity	NPC164649
0.9035	High Similarity	NPC48342
0.8992	High Similarity	NPC325294
0.8992	High Similarity	NPC321822
0.8991	High Similarity	NPC11554
0.8981	High Similarity	NPC21594
0.8974	High Similarity	NPC471794
0.8966	High Similarity	NPC328504
0.8957	High Similarity	NPC151197
0.8947	High Similarity	NPC16030
0.8938	High Similarity	NPC469719
0.8919	High Similarity	NPC151537
0.8919	High Similarity	NPC322753
0.8919	High Similarity	NPC77772
0.8917	High Similarity	NPC471077
0.8909	High Similarity	NPC58865
0.8908	High Similarity	NPC137750
0.8898	High Similarity	NPC198014
0.8889	High Similarity	NPC249340
0.8889	High Similarity	NPC162935
0.8889	High Similarity	NPC253627
0.886	High Similarity	NPC474387
0.886	High Similarity	NPC247858
0.886	High Similarity	NPC474358
0.886	High Similarity	NPC257540
0.886	High Similarity	NPC137496
0.886	High Similarity	NPC154511
0.8833	High Similarity	NPC100414
0.8833	High Similarity	NPC43000
0.8814	High Similarity	NPC71094
0.8814	High Similarity	NPC152946
0.8803	High Similarity	NPC259703
0.8803	High Similarity	NPC32322
0.8761	High Similarity	NPC317869
0.876	High Similarity	NPC108164
0.875	High Similarity	NPC87985
0.875	High Similarity	NPC124030
0.875	High Similarity	NPC470770
0.875	High Similarity	NPC4286
0.875	High Similarity	NPC266937
0.875	High Similarity	NPC76119
0.8739	High Similarity	NPC314187
0.8729	High Similarity	NPC142198
0.8729	High Similarity	NPC77569
0.8729	High Similarity	NPC154696
0.8727	High Similarity	NPC472979
0.8727	High Similarity	NPC27252
0.8716	High Similarity	NPC243601
0.8707	High Similarity	NPC206
0.8696	High Similarity	NPC141001
0.8692	High Similarity	NPC211885
0.8684	High Similarity	NPC471534
0.8673	High Similarity	NPC62867
0.8673	High Similarity	NPC177962
0.8673	High Similarity	NPC302371
0.8673	High Similarity	NPC471179
0.8655	High Similarity	NPC478058
0.8655	High Similarity	NPC321402
0.8655	High Similarity	NPC176208
0.8655	High Similarity	NPC121168
0.8649	High Similarity	NPC149455
0.8649	High Similarity	NPC64642
0.8649	High Similarity	NPC472982
0.8644	High Similarity	NPC241001
0.8636	High Similarity	NPC271274
0.8629	High Similarity	NPC471851
0.8624	High Similarity	NPC475225
0.8621	High Similarity	NPC299180
0.8607	High Similarity	NPC186889
0.8607	High Similarity	NPC476536
0.8596	High Similarity	NPC322239
0.8559	High Similarity	NPC472980
0.8559	High Similarity	NPC68339
0.8559	High Similarity	NPC478121
0.8559	High Similarity	NPC320439
0.8532	High Similarity	NPC19856
0.8532	High Similarity	NPC235762
0.8532	High Similarity	NPC471228
0.8525	High Similarity	NPC71610
0.8519	High Similarity	NPC225506
0.85	High Similarity	NPC297057
0.8496	Intermediate Similarity	NPC296683
0.8492	Intermediate Similarity	NPC78307
0.8482	Intermediate Similarity	NPC262365
0.848	Intermediate Similarity	NPC312341
0.8475	Intermediate Similarity	NPC42657
0.8475	Intermediate Similarity	NPC323074
0.8455	Intermediate Similarity	NPC176130
0.8455	Intermediate Similarity	NPC78364
0.8455	Intermediate Similarity	NPC272029
0.8455	Intermediate Similarity	NPC238696
0.8455	Intermediate Similarity	NPC69424
0.8455	Intermediate Similarity	NPC84672
0.8448	Intermediate Similarity	NPC84999
0.8448	Intermediate Similarity	NPC474486
0.8448	Intermediate Similarity	NPC246760
0.844	Intermediate Similarity	NPC252105
0.8435	Intermediate Similarity	NPC263753
0.8426	Intermediate Similarity	NPC128723
0.8426	Intermediate Similarity	NPC299762
0.8426	Intermediate Similarity	NPC122005
0.8426	Intermediate Similarity	NPC252821
0.8426	Intermediate Similarity	NPC33675
0.8425	Intermediate Similarity	NPC202225
0.8421	Intermediate Similarity	NPC469912
0.8417	Intermediate Similarity	NPC475166
0.8417	Intermediate Similarity	NPC474115
0.8413	Intermediate Similarity	NPC321086
0.8413	Intermediate Similarity	NPC85595
0.8403	Intermediate Similarity	NPC325544
0.8403	Intermediate Similarity	NPC99734
0.8403	Intermediate Similarity	NPC318581
0.8403	Intermediate Similarity	NPC318552
0.8403	Intermediate Similarity	NPC190501
0.8403	Intermediate Similarity	NPC477037
0.8403	Intermediate Similarity	NPC103916
0.84	Intermediate Similarity	NPC196193
0.84	Intermediate Similarity	NPC249425
0.8393	Intermediate Similarity	NPC66834
0.8387	Intermediate Similarity	NPC201069
0.8387	Intermediate Similarity	NPC3009
0.8378	Intermediate Similarity	NPC47284
0.8378	Intermediate Similarity	NPC219286
0.8378	Intermediate Similarity	NPC138942
0.8378	Intermediate Similarity	NPC99557
0.8376	Intermediate Similarity	NPC312105
0.8364	Intermediate Similarity	NPC168829
0.8364	Intermediate Similarity	NPC269212
0.8362	Intermediate Similarity	NPC107240
0.8362	Intermediate Similarity	NPC249270
0.8349	Intermediate Similarity	NPC72729
0.8349	Intermediate Similarity	NPC174911
0.8348	Intermediate Similarity	NPC473521
0.8346	Intermediate Similarity	NPC477139
0.8346	Intermediate Similarity	NPC49742
0.8346	Intermediate Similarity	NPC227719
0.8333	Intermediate Similarity	NPC44732
0.8333	Intermediate Similarity	NPC129176
0.8333	Intermediate Similarity	NPC79241
0.8333	Intermediate Similarity	NPC6597
0.8333	Intermediate Similarity	NPC291001
0.8333	Intermediate Similarity	NPC224870
0.8333	Intermediate Similarity	NPC476847
0.8333	Intermediate Similarity	NPC77492
0.832	Intermediate Similarity	NPC276238
0.8319	Intermediate Similarity	NPC176893
0.8318	Intermediate Similarity	NPC144682
0.8318	Intermediate Similarity	NPC222146
0.8306	Intermediate Similarity	NPC262936
0.8306	Intermediate Similarity	NPC72667
0.8306	Intermediate Similarity	NPC30491
0.8304	Intermediate Similarity	NPC53740
0.8288	Intermediate Similarity	NPC288411
0.8288	Intermediate Similarity	NPC323810
0.8276	Intermediate Similarity	NPC321589
0.8276	Intermediate Similarity	NPC319803
0.8276	Intermediate Similarity	NPC117846
0.8273	Intermediate Similarity	NPC51015
0.8268	Intermediate Similarity	NPC59239
0.8268	Intermediate Similarity	NPC165612
0.8261	Intermediate Similarity	NPC308689
0.8257	Intermediate Similarity	NPC92730

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 NPC35797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	944
0.2-0.3	1308
0.3-0.4	2835
0.4-0.5	2032
0.5-0.6	1230
0.6-0.7	421
0.7-0.8	95
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9035	High Similarity	NPD3091	Approved
0.8729	High Similarity	NPD3092	Approved
0.8559	High Similarity	NPD2342	Discontinued
0.8559	High Similarity	NPD3095	Discontinued
0.8509	High Similarity	NPD7635	Approved
0.8443	Intermediate Similarity	NPD3094	Phase 2
0.8403	Intermediate Similarity	NPD4059	Approved
0.8403	Intermediate Similarity	NPD3019	Approved
0.8318	Intermediate Similarity	NPD1809	Phase 2
0.8257	Intermediate Similarity	NPD3020	Approved
0.825	Intermediate Similarity	NPD2932	Approved
0.8241	Intermediate Similarity	NPD288	Approved
0.816	Intermediate Similarity	NPD5736	Approved
0.8148	Intermediate Similarity	NPD844	Approved
0.8087	Intermediate Similarity	NPD4750	Phase 3
0.8056	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4097	Suspended
0.7984	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3620	Phase 2
0.7984	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2859	Approved
0.7982	Intermediate Similarity	NPD2860	Approved
0.7963	Intermediate Similarity	NPD845	Approved
0.7951	Intermediate Similarity	NPD2286	Discontinued
0.7949	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3022	Approved
0.7931	Intermediate Similarity	NPD3021	Approved
0.7907	Intermediate Similarity	NPD6663	Approved
0.789	Intermediate Similarity	NPD2934	Approved
0.789	Intermediate Similarity	NPD2933	Approved
0.7869	Intermediate Similarity	NPD4093	Discontinued
0.7815	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4626	Approved
0.7805	Intermediate Similarity	NPD1751	Approved
0.7795	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4624	Approved
0.7744	Intermediate Similarity	NPD7742	Approved
0.7744	Intermediate Similarity	NPD7743	Approved
0.7742	Intermediate Similarity	NPD3023	Approved
0.7742	Intermediate Similarity	NPD3026	Approved
0.7724	Intermediate Similarity	NPD3024	Approved
0.7724	Intermediate Similarity	NPD3025	Approved
0.7719	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4140	Approved
0.7698	Intermediate Similarity	NPD5327	Phase 3
0.7692	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2606	Approved
0.7674	Intermediate Similarity	NPD2605	Approved
0.7667	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5735	Approved
0.7623	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5155	Approved
0.7615	Intermediate Similarity	NPD5156	Approved
0.7597	Intermediate Similarity	NPD3637	Approved
0.7597	Intermediate Similarity	NPD3636	Approved
0.7597	Intermediate Similarity	NPD3635	Approved
0.7581	Intermediate Similarity	NPD5691	Approved
0.7576	Intermediate Similarity	NPD4060	Phase 1
0.7538	Intermediate Similarity	NPD3595	Approved
0.7538	Intermediate Similarity	NPD3594	Approved
0.752	Intermediate Similarity	NPD4589	Approved
0.7519	Intermediate Similarity	NPD2194	Approved
0.7519	Intermediate Similarity	NPD2195	Approved
0.7518	Intermediate Similarity	NPD3638	Discontinued
0.75	Intermediate Similarity	NPD6696	Suspended
0.7481	Intermediate Similarity	NPD4625	Phase 3
0.7479	Intermediate Similarity	NPD1792	Phase 2
0.7478	Intermediate Similarity	NPD846	Approved
0.7478	Intermediate Similarity	NPD940	Approved
0.7463	Intermediate Similarity	NPD6353	Approved
0.7459	Intermediate Similarity	NPD497	Approved
0.7424	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1201	Approved
0.7377	Intermediate Similarity	NPD498	Approved
0.7377	Intermediate Similarity	NPD496	Approved
0.7377	Intermediate Similarity	NPD495	Approved
0.7377	Intermediate Similarity	NPD2229	Approved
0.7377	Intermediate Similarity	NPD2228	Approved
0.7377	Intermediate Similarity	NPD2234	Approved
0.7364	Intermediate Similarity	NPD1283	Approved
0.736	Intermediate Similarity	NPD5304	Approved
0.736	Intermediate Similarity	NPD5303	Approved
0.7339	Intermediate Similarity	NPD7340	Approved
0.7338	Intermediate Similarity	NPD7003	Approved
0.7328	Intermediate Similarity	NPD2861	Phase 2
0.7308	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1651	Approved
0.7287	Intermediate Similarity	NPD4749	Approved
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7266	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3645	Discontinued
0.7254	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4726	Approved
0.7246	Intermediate Similarity	NPD4725	Approved
0.7246	Intermediate Similarity	NPD4721	Approved
0.7244	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1242	Phase 1
0.7236	Intermediate Similarity	NPD1398	Phase 1
0.7227	Intermediate Similarity	NPD1445	Approved
0.7227	Intermediate Similarity	NPD1444	Approved
0.7226	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD111	Approved
0.7222	Intermediate Similarity	NPD7330	Discontinued
0.7222	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD8166	Discontinued
0.7183	Intermediate Similarity	NPD7041	Phase 2
0.7183	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1470	Approved
0.7174	Intermediate Similarity	NPD5408	Approved
0.7174	Intermediate Similarity	NPD5406	Approved
0.7174	Intermediate Similarity	NPD5404	Approved
0.7174	Intermediate Similarity	NPD5405	Approved
0.7165	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7133	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3657	Discovery
0.7132	Intermediate Similarity	NPD1610	Phase 2
0.7132	Intermediate Similarity	NPD1281	Approved
0.7121	Intermediate Similarity	NPD6584	Phase 3
0.712	Intermediate Similarity	NPD6671	Approved
0.712	Intermediate Similarity	NPD7157	Approved
0.7101	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8651	Approved
0.7097	Intermediate Similarity	NPD5283	Phase 1
0.7087	Intermediate Similarity	NPD7741	Discontinued
0.7077	Intermediate Similarity	NPD2230	Approved
0.7077	Intermediate Similarity	NPD2233	Approved
0.7077	Intermediate Similarity	NPD2232	Approved
0.7071	Intermediate Similarity	NPD7037	Approved
0.7068	Intermediate Similarity	NPD4208	Discontinued
0.7063	Intermediate Similarity	NPD7390	Discontinued
0.7054	Intermediate Similarity	NPD3143	Discontinued
0.705	Intermediate Similarity	NPD6099	Approved
0.705	Intermediate Similarity	NPD6100	Approved
0.7042	Intermediate Similarity	NPD8131	Suspended
0.704	Intermediate Similarity	NPD5951	Approved
0.7037	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4659	Approved
0.7023	Intermediate Similarity	NPD1669	Approved
0.6985	Remote Similarity	NPD8032	Phase 2
0.6975	Remote Similarity	NPD9500	Approved
0.6967	Remote Similarity	NPD2684	Approved
0.6966	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2157	Approved
0.6949	Remote Similarity	NPD3028	Approved
0.6947	Remote Similarity	NPD3070	Discontinued
0.6944	Remote Similarity	NPD2420	Approved
0.6944	Remote Similarity	NPD2421	Approved
0.6935	Remote Similarity	NPD228	Approved
0.6934	Remote Similarity	NPD2238	Phase 2
0.6934	Remote Similarity	NPD3109	Approved
0.6934	Remote Similarity	NPD3110	Approved
0.6934	Remote Similarity	NPD2979	Phase 3
0.6929	Remote Similarity	NPD7636	Approved
0.6923	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5699	Approved
0.6917	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4103	Phase 2
0.6912	Remote Similarity	NPD7294	Phase 1
0.6911	Remote Similarity	NPD5451	Approved
0.6905	Remote Similarity	NPD1793	Approved
0.6905	Remote Similarity	NPD1791	Approved
0.6894	Remote Similarity	NPD6583	Phase 3
0.6894	Remote Similarity	NPD6582	Phase 2
0.6879	Remote Similarity	NPD5762	Approved
0.6879	Remote Similarity	NPD5763	Approved
0.6879	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1611	Approved
0.6861	Remote Similarity	NPD6405	Approved
0.6861	Remote Similarity	NPD6407	Approved
0.6857	Remote Similarity	NPD4108	Discontinued
0.685	Remote Similarity	NPD4198	Discontinued
0.685	Remote Similarity	NPD709	Approved
0.6849	Remote Similarity	NPD6090	Discontinued
0.6846	Remote Similarity	NPD7725	Approved
0.6846	Remote Similarity	NPD1778	Approved
0.6846	Remote Similarity	NPD2668	Approved
0.6846	Remote Similarity	NPD2667	Approved
0.6838	Remote Similarity	NPD3027	Phase 3
0.6838	Remote Similarity	NPD7095	Approved
0.6831	Remote Similarity	NPD4256	Phase 2
0.6831	Remote Similarity	NPD4257	Approved
0.6824	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7458	Discontinued
0.6822	Remote Similarity	NPD1548	Phase 1
0.6797	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1133	Approved
0.6791	Remote Similarity	NPD1129	Approved
0.6791	Remote Similarity	NPD1135	Approved
0.6791	Remote Similarity	NPD1134	Approved
0.6791	Remote Similarity	NPD1131	Approved
0.6788	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2209	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