NPASS Compound

Structure

CID84672 OpenBabel06191715422D 21 23 0 0 1 0 0 0 0 0999 V2000 -4.3301 4.5000 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 -0.5000 -0.8660 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 0.8660 1.5000 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 0.8660 0.5000 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 3.0000 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 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -1.7321 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 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 19 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 6 1 1 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 15 18 1 0 0 0 0 16 10 1 6 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.19
Volume:	318.545
LogP:	5.391
LogD:	4.744
LogS:	-5.099
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	3.491
Fsp3:	0.632
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:	-4.742
MDCK Permeability:	1.5787616575835273e-05
Pgp-inhibitor:	0.719
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.603
Plasma Protein Binding (PPB):	98.57872009277344%
Volume Distribution (VD):	0.999
Pgp-substrate:	3.0563228130340576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.339
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.549
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.554
CYP2D6-substrate:	0.703
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	3.949
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.751
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.251
Carcinogencity:	0.074
Eye Corrosion:	0.004
Eye Irritation:	0.769
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC84672

Natural Product ID:	NPC84672
*Common Name:**	(-)-(5R,10S)-12-Hydroxy-7-Oxo-20-Norabieta-8,11,13-Triene
IUPAC Name:	(4aS,10aR)-6-hydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,4a,10,10a-hexahydrophenanthren-9-one
Synonyms:
Standard InCHIKey:	CCEWUJMXSVJXEO-MLGOLLRUSA-N
Standard InCHI:	InChI=1S/C19H26O2/c1-11(2)13-8-15-14(9-17(13)20)12-6-5-7-19(3,4)16(12)10-18(15)21/h8-9,11-12,16,20H,5-7,10H2,1-4H3/t12-,16-/m1/s1
SMILES:	O=C1C[C@@H]2[C@@H](c3c1cc(C(C)C)c(c3)O)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651072
PubChem CID:	50900598
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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ 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	5
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[518717]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[518717]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[518717]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[518717]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[518717]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	56.1	%	PMID[518717]

☑ 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 NPC84672 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	324
0.1-0.2	1584
0.2-0.3	3022
0.3-0.4	8140
0.4-0.5	10591
0.5-0.6	6955
0.6-0.7	8826
0.7-0.8	2800
0.8-0.85	327
0.85-0.9	93
0.9-0.95	19
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC176130
1.0	High Similarity	NPC78364
1.0	High Similarity	NPC69424
0.9835	High Similarity	NPC72667
0.9756	High Similarity	NPC108129
0.9752	High Similarity	NPC254492
0.9677	High Similarity	NPC471851
0.9675	High Similarity	NPC276238
0.9675	High Similarity	NPC171460
0.9675	High Similarity	NPC303910
0.9587	High Similarity	NPC199273
0.9524	High Similarity	NPC78307
0.9524	High Similarity	NPC477139
0.9449	High Similarity	NPC202225
0.9435	High Similarity	NPC3009
0.9435	High Similarity	NPC96024
0.9421	High Similarity	NPC282577
0.937	High Similarity	NPC111845
0.9339	High Similarity	NPC154696
0.9231	High Similarity	NPC475957
0.9219	High Similarity	NPC138472
0.9194	High Similarity	NPC123506
0.9194	High Similarity	NPC137750
0.9106	High Similarity	NPC176208
0.9098	High Similarity	NPC32322
0.9098	High Similarity	NPC259703
0.9077	High Similarity	NPC153088
0.9032	High Similarity	NPC471187
0.9024	High Similarity	NPC249340
0.9024	High Similarity	NPC162935
0.8976	High Similarity	NPC229894
0.896	High Similarity	NPC181334
0.8952	High Similarity	NPC11250
0.8939	High Similarity	NPC36868
0.8915	High Similarity	NPC164295
0.8915	High Similarity	NPC18798
0.8906	High Similarity	NPC117899
0.8881	High Similarity	NPC471853
0.888	High Similarity	NPC273683
0.888	High Similarity	NPC275145
0.8872	High Similarity	NPC230811
0.8871	High Similarity	NPC120545
0.8864	High Similarity	NPC471670
0.8828	High Similarity	NPC193203
0.8828	High Similarity	NPC48248
0.8824	High Similarity	NPC100242
0.8819	High Similarity	NPC71610
0.88	High Similarity	NPC91478
0.8797	High Similarity	NPC277559
0.8797	High Similarity	NPC53001
0.8797	High Similarity	NPC49911
0.879	High Similarity	NPC241001
0.8788	High Similarity	NPC477596
0.8769	High Similarity	NPC476847
0.8769	High Similarity	NPC93015
0.8769	High Similarity	NPC239134
0.875	High Similarity	NPC248068
0.875	High Similarity	NPC308572
0.8741	High Similarity	NPC169452
0.8741	High Similarity	NPC181560
0.8731	High Similarity	NPC87723
0.873	High Similarity	NPC198014
0.8722	High Similarity	NPC191976
0.8722	High Similarity	NPC472308
0.872	High Similarity	NPC253627
0.8712	High Similarity	NPC50924
0.8712	High Similarity	NPC12070
0.8712	High Similarity	NPC477594
0.871	High Similarity	NPC190501
0.871	High Similarity	NPC318552
0.8672	High Similarity	NPC15837
0.8667	High Similarity	NPC138099
0.8667	High Similarity	NPC242994
0.8661	High Similarity	NPC142956
0.8661	High Similarity	NPC173978
0.8657	High Similarity	NPC471905
0.8651	High Similarity	NPC121168
0.8647	High Similarity	NPC283088
0.8647	High Similarity	NPC249272
0.8647	High Similarity	NPC80035
0.864	High Similarity	NPC190971
0.8636	High Similarity	NPC267205
0.8636	High Similarity	NPC114183
0.8636	High Similarity	NPC225051
0.8636	High Similarity	NPC49742
0.8636	High Similarity	NPC115458
0.8636	High Similarity	NPC52407
0.8629	High Similarity	NPC42657
0.8626	High Similarity	NPC41847
0.8626	High Similarity	NPC72669
0.8626	High Similarity	NPC474517
0.8626	High Similarity	NPC291001
0.8623	High Similarity	NPC196941
0.8623	High Similarity	NPC309169
0.8615	High Similarity	NPC99731
0.8613	High Similarity	NPC193555
0.8613	High Similarity	NPC477209
0.8607	High Similarity	NPC322197
0.8605	High Similarity	NPC19432
0.8603	High Similarity	NPC476534
0.8595	High Similarity	NPC242136
0.8594	High Similarity	NPC87985
0.8593	High Similarity	NPC4214
0.8593	High Similarity	NPC13715
0.8583	High Similarity	NPC260323
0.8583	High Similarity	NPC176279
0.8582	High Similarity	NPC254847
0.8582	High Similarity	NPC474311
0.8571	High Similarity	NPC270899
0.8571	High Similarity	NPC5568
0.8561	High Similarity	NPC478160
0.8561	High Similarity	NPC165612
0.856	High Similarity	NPC478121
0.855	High Similarity	NPC253488
0.8538	High Similarity	NPC282923
0.8527	High Similarity	NPC474737
0.8527	High Similarity	NPC160499
0.8519	High Similarity	NPC477592
0.8519	High Similarity	NPC53414
0.8519	High Similarity	NPC53206
0.8516	High Similarity	NPC164014
0.8512	High Similarity	NPC231717
0.8507	High Similarity	NPC258502
0.8504	High Similarity	NPC300274
0.8504	High Similarity	NPC307174
0.85	High Similarity	NPC143685
0.8496	Intermediate Similarity	NPC53896
0.8496	Intermediate Similarity	NPC4170
0.8496	Intermediate Similarity	NPC59459
0.8485	Intermediate Similarity	NPC244699
0.8485	Intermediate Similarity	NPC17083
0.8478	Intermediate Similarity	NPC184935
0.8478	Intermediate Similarity	NPC135524
0.8478	Intermediate Similarity	NPC19631
0.8478	Intermediate Similarity	NPC239136
0.8473	Intermediate Similarity	NPC25736
0.8473	Intermediate Similarity	NPC146647
0.8473	Intermediate Similarity	NPC34414
0.8468	Intermediate Similarity	NPC174087
0.8462	Intermediate Similarity	NPC471530
0.8456	Intermediate Similarity	NPC471974
0.8456	Intermediate Similarity	NPC477593
0.8456	Intermediate Similarity	NPC61398
0.8456	Intermediate Similarity	NPC469680
0.8456	Intermediate Similarity	NPC469681
0.8456	Intermediate Similarity	NPC416
0.8455	Intermediate Similarity	NPC192948
0.8455	Intermediate Similarity	NPC35797
0.8444	Intermediate Similarity	NPC7464
0.8444	Intermediate Similarity	NPC155211
0.8444	Intermediate Similarity	NPC272268
0.844	Intermediate Similarity	NPC52692
0.8438	Intermediate Similarity	NPC174991
0.8438	Intermediate Similarity	NPC375356
0.8433	Intermediate Similarity	NPC472262
0.8433	Intermediate Similarity	NPC161964
0.8433	Intermediate Similarity	NPC282780
0.8433	Intermediate Similarity	NPC287604
0.8433	Intermediate Similarity	NPC166480
0.8433	Intermediate Similarity	NPC293454
0.8429	Intermediate Similarity	NPC12402
0.8421	Intermediate Similarity	NPC58685
0.8421	Intermediate Similarity	NPC183103
0.8417	Intermediate Similarity	NPC478164
0.8417	Intermediate Similarity	NPC174905
0.8417	Intermediate Similarity	NPC474203
0.8417	Intermediate Similarity	NPC295712
0.8417	Intermediate Similarity	NPC451542
0.8417	Intermediate Similarity	NPC313047
0.8417	Intermediate Similarity	NPC293545
0.8409	Intermediate Similarity	NPC199253
0.8409	Intermediate Similarity	NPC136588
0.8409	Intermediate Similarity	NPC27659
0.8406	Intermediate Similarity	NPC246638
0.8406	Intermediate Similarity	NPC305845
0.8406	Intermediate Similarity	NPC204045
0.8397	Intermediate Similarity	NPC234175
0.8394	Intermediate Similarity	NPC143438
0.8387	Intermediate Similarity	NPC38893
0.8387	Intermediate Similarity	NPC471668
0.8387	Intermediate Similarity	NPC308311
0.8387	Intermediate Similarity	NPC477453
0.8387	Intermediate Similarity	NPC477137
0.8385	Intermediate Similarity	NPC3224
0.8374	Intermediate Similarity	NPC195922
0.8372	Intermediate Similarity	NPC68756
0.8372	Intermediate Similarity	NPC15127
0.8372	Intermediate Similarity	NPC152525
0.837	Intermediate Similarity	NPC22644
0.837	Intermediate Similarity	NPC290803
0.8369	Intermediate Similarity	NPC477208
0.8361	Intermediate Similarity	NPC250323
0.8358	Intermediate Similarity	NPC314048
0.8358	Intermediate Similarity	NPC294226
0.8347	Intermediate Similarity	NPC141782
0.8346	Intermediate Similarity	NPC216216
0.8346	Intermediate Similarity	NPC472981
0.8346	Intermediate Similarity	NPC85342
0.8346	Intermediate Similarity	NPC205992
0.8345	Intermediate Similarity	NPC201297

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 NPC84672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	966
0.2-0.3	1239
0.3-0.4	2582
0.4-0.5	2287
0.5-0.6	1200
0.6-0.7	457
0.7-0.8	84
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD3019	Approved
0.8629	High Similarity	NPD4196	Clinical (unspecified phase)
0.8582	High Similarity	NPD1509	Clinical (unspecified phase)
0.856	High Similarity	NPD2932	Approved
0.8425	Intermediate Similarity	NPD1201	Approved
0.8308	Intermediate Similarity	NPD1470	Approved
0.8227	Intermediate Similarity	NPD7390	Discontinued
0.8143	Intermediate Similarity	NPD7003	Approved
0.8116	Intermediate Similarity	NPD5406	Approved
0.8116	Intermediate Similarity	NPD5405	Approved
0.8116	Intermediate Similarity	NPD5404	Approved
0.8116	Intermediate Similarity	NPD5408	Approved
0.808	Intermediate Similarity	NPD5951	Approved
0.8062	Intermediate Similarity	NPD3026	Approved
0.8062	Intermediate Similarity	NPD3023	Approved
0.8047	Intermediate Similarity	NPD3025	Approved
0.8047	Intermediate Similarity	NPD3024	Approved
0.7953	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD7458	Discontinued
0.781	Intermediate Similarity	NPD6663	Approved
0.7803	Intermediate Similarity	NPD3972	Approved
0.7793	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5736	Approved
0.771	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3091	Approved
0.7661	Intermediate Similarity	NPD2342	Discontinued
0.766	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD8166	Discontinued
0.7638	Intermediate Similarity	NPD7635	Approved
0.763	Intermediate Similarity	NPD1164	Approved
0.7606	Intermediate Similarity	NPD6099	Approved
0.7606	Intermediate Similarity	NPD6100	Approved
0.7576	Intermediate Similarity	NPD4059	Approved
0.7556	Intermediate Similarity	NPD1283	Approved
0.7552	Intermediate Similarity	NPD2346	Discontinued
0.7534	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7482	Intermediate Similarity	NPD3764	Approved
0.7467	Intermediate Similarity	NPD3226	Approved
0.7463	Intermediate Similarity	NPD3092	Approved
0.7448	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2798	Approved
0.7444	Intermediate Similarity	NPD4626	Approved
0.7444	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1809	Phase 2
0.7413	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD1607	Approved
0.7381	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3020	Approved
0.7358	Intermediate Similarity	NPD7473	Discontinued
0.7355	Intermediate Similarity	NPD288	Approved
0.7353	Intermediate Similarity	NPD1755	Approved
0.7351	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7610	Discontinued
0.7333	Intermediate Similarity	NPD1281	Approved
0.7325	Intermediate Similarity	NPD6959	Discontinued
0.7323	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3095	Discontinued
0.731	Intermediate Similarity	NPD2344	Approved
0.7305	Intermediate Similarity	NPD8032	Phase 2
0.7299	Intermediate Similarity	NPD1876	Approved
0.7292	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7008	Discontinued
0.7286	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4628	Phase 3
0.7279	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4878	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD844	Approved
0.7266	Intermediate Similarity	NPD4750	Phase 3
0.726	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1240	Approved
0.7246	Intermediate Similarity	NPD3094	Phase 2
0.723	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3495	Discontinued
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD1929	Approved
0.72	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1930	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.72	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2286	Discontinued
0.7177	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1510	Phase 2
0.7164	Intermediate Similarity	NPD9545	Approved
0.7162	Intermediate Similarity	NPD3750	Approved
0.7153	Intermediate Similarity	NPD4097	Suspended
0.7132	Intermediate Similarity	NPD3021	Approved
0.7132	Intermediate Similarity	NPD3022	Approved
0.7131	Intermediate Similarity	NPD2860	Approved
0.7131	Intermediate Similarity	NPD2859	Approved
0.7115	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2309	Approved
0.7111	Intermediate Similarity	NPD5691	Approved
0.7111	Intermediate Similarity	NPD4093	Discontinued
0.7107	Intermediate Similarity	NPD845	Approved
0.7101	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2066	Phase 3
0.7077	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1751	Approved
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.7054	Intermediate Similarity	NPD74	Approved
0.7054	Intermediate Similarity	NPD9266	Approved
0.7051	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2933	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7034	Intermediate Similarity	NPD6651	Approved
0.7023	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4208	Discontinued
0.7015	Intermediate Similarity	NPD9493	Approved
0.7014	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD2797	Approved
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.698	Remote Similarity	NPD2800	Approved
0.6977	Remote Similarity	NPD9263	Approved
0.6977	Remote Similarity	NPD9267	Approved
0.6977	Remote Similarity	NPD9264	Approved
0.6974	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2605	Approved
0.6972	Remote Similarity	NPD2606	Approved
0.6968	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD7236	Approved
0.6951	Remote Similarity	NPD6020	Phase 2
0.695	Remote Similarity	NPD4624	Approved
0.6939	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD7411	Suspended
0.6923	Remote Similarity	NPD5156	Approved
0.6923	Remote Similarity	NPD5155	Approved
0.6913	Remote Similarity	NPD1549	Phase 2
0.6912	Remote Similarity	NPD7009	Phase 2
0.6906	Remote Similarity	NPD9269	Phase 2
0.6906	Remote Similarity	NPD1608	Approved
0.6901	Remote Similarity	NPD3635	Approved
0.6901	Remote Similarity	NPD9494	Approved
0.6901	Remote Similarity	NPD3636	Approved
0.6901	Remote Similarity	NPD3637	Approved
0.6897	Remote Similarity	NPD4060	Phase 1
0.6897	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4140	Approved
0.6897	Remote Similarity	NPD3620	Phase 2
0.6894	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2796	Approved
0.689	Remote Similarity	NPD7177	Discontinued
0.6889	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4879	Approved
0.6875	Remote Similarity	NPD1237	Approved
0.6861	Remote Similarity	NPD9268	Approved
0.6859	Remote Similarity	NPD6599	Discontinued
0.6853	Remote Similarity	NPD3594	Approved
0.6853	Remote Similarity	NPD3595	Approved
0.6853	Remote Similarity	NPD4207	Discontinued
0.6846	Remote Similarity	NPD1471	Phase 3
0.6846	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7239	Suspended
0.6831	Remote Similarity	NPD2194	Approved
0.6831	Remote Similarity	NPD2195	Approved
0.6824	Remote Similarity	NPD3748	Approved
0.6824	Remote Similarity	NPD8150	Discontinued
0.6813	Remote Similarity	NPD3749	Approved
0.6813	Remote Similarity	NPD7075	Discontinued
0.6812	Remote Similarity	NPD4589	Approved
0.6809	Remote Similarity	NPD6696	Suspended
0.6806	Remote Similarity	NPD4625	Phase 3
0.6797	Remote Similarity	NPD1511	Approved
0.6792	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2531	Phase 2
0.6779	Remote Similarity	NPD4477	Approved
0.6779	Remote Similarity	NPD4476	Approved
0.6779	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD1934	Approved
0.6768	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7028	Phase 2
0.675	Remote Similarity	NPD7768	Phase 2
0.675	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1792	Phase 2
0.6741	Remote Similarity	NPD2629	Approved
0.6741	Remote Similarity	NPD497	Approved
0.6738	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5327	Phase 3
0.6735	Remote Similarity	NPD230	Phase 1
0.673	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2801	Approved
0.6719	Remote Similarity	NPD846	Approved
0.6719	Remote Similarity	NPD940	Approved
0.6719	Remote Similarity	NPD1932	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