NPASS Compound

Structure

NPC469599 OpenBabel07101718182D 37 40 0 0 1 0 0 0 0 0999 V2000 -1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 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 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 3.1622 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 4.1132 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 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 1.7321 -1.0000 0.0000 C 0 0 1 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 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4743 5.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 22 2 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 32 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 6 0 0 0 19 27 1 0 0 0 0 19 29 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 34 2 0 0 0 0 21 37 1 0 0 0 0 22 30 1 0 0 0 0 23 36 1 6 0 0 0 24 9 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 30 1 6 0 0 0 26 31 1 6 0 0 0 27 35 2 0 0 0 0 28 29 1 0 0 0 0 28 37 1 6 0 0 0 29 31 1 6 0 0 0 30 5 1 6 0 0 0 31 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.35
Volume:	552.702
LogP:	4.666
LogD:	3.843
LogS:	-4.7
# Rotatable Bonds:	10
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	4.875
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
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:	-4.638
MDCK Permeability:	3.884852412738837e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.417

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.419
Plasma Protein Binding (PPB):	89.8912353515625%
Volume Distribution (VD):	1.116
Pgp-substrate:	2.7296228408813477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.279
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	5.197
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.804
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.948
Carcinogencity:	0.722
Eye Corrosion:	0.005
Eye Irritation:	0.02
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC469599

Natural Product ID:	NPC469599
*Common Name:**	(25R)-26-Hydroxy-22-Oxocholest-5-En-3Beta,16Beta-Diyldiacetate
IUPAC Name:	[(3S,8S,9S,10R,13S,14S,16S,17R)-16-acetyloxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	INUVWOFKWFJJFJ-WLMGVJRSSA-N
Standard InCHI:	InChI=1S/C31H48O6/c1-18(17-32)7-10-27(35)19(2)29-28(37-21(4)34)16-26-24-9-8-22-15-23(36-20(3)33)11-13-30(22,5)25(24)12-14-31(26,29)6/h8,18-19,23-26,28-29,32H,7,9-17H2,1-6H3/t18-,19-,23+,24-,25+,26+,28+,29+,30+,31+/m1/s1
SMILES:	OC[C@@H](CCC(=O)[C@H]([C@H]1[C@@H](OC(=O)C)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1093269
PubChem CID:	14769377
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols and derivatives

*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
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	roots	sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA)	n.a.	PMID[22880631]

☑ 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	8
Others	2

Activity Type	# Activity
Cell Line	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2306	Cell Line	Ca-Ski	Homo sapiens	IC50	=	47100.0	nM	PMID[557437]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	76.15	%	PMID[557437]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	23.85	%	PMID[557437]
NPT2306	Cell Line	Ca-Ski	Homo sapiens	IC50	=	33900.0	nM	PMID[557438]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[557439]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[557439]
NPT1524	Cell Line	MM96L	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[557439]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[557439]
NPT1523	Cell Line	NFF	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[557439]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.8	ug.mL-1	PMID[557439]

☑ 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 NPC469599 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	176
0.1-0.2	1087
0.2-0.3	4688
0.3-0.4	12842
0.4-0.5	8713
0.5-0.6	5719
0.6-0.7	5870
0.7-0.8	3023
0.8-0.85	458
0.85-0.9	113
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9438	High Similarity	NPC154101
0.914	High Similarity	NPC475894
0.9121	High Similarity	NPC470376
0.9121	High Similarity	NPC470375
0.9091	High Similarity	NPC155011
0.9053	High Similarity	NPC474327
0.9	High Similarity	NPC477943
0.9	High Similarity	NPC54689
0.8977	High Similarity	NPC474218
0.8947	High Similarity	NPC218383
0.8936	High Similarity	NPC107243
0.8936	High Similarity	NPC57416
0.8925	High Similarity	NPC69548
0.8925	High Similarity	NPC184848
0.8913	High Similarity	NPC170220
0.8913	High Similarity	NPC107674
0.8913	High Similarity	NPC66429
0.8913	High Similarity	NPC141497
0.8913	High Similarity	NPC152897
0.8913	High Similarity	NPC470224
0.8913	High Similarity	NPC206810
0.8901	High Similarity	NPC471896
0.8889	High Similarity	NPC28227
0.8889	High Similarity	NPC294480
0.8889	High Similarity	NPC328313
0.8878	High Similarity	NPC231530
0.8878	High Similarity	NPC278628
0.8866	High Similarity	NPC140723
0.8864	High Similarity	NPC221758
0.8864	High Similarity	NPC82902
0.8864	High Similarity	NPC59453
0.8842	High Similarity	NPC477813
0.8842	High Similarity	NPC477854
0.883	High Similarity	NPC173272
0.883	High Similarity	NPC42042
0.8817	High Similarity	NPC159410
0.8804	High Similarity	NPC23434
0.8804	High Similarity	NPC212301
0.8804	High Similarity	NPC110657
0.8804	High Similarity	NPC26888
0.8804	High Similarity	NPC297265
0.8804	High Similarity	NPC86266
0.8791	High Similarity	NPC474570
0.8791	High Similarity	NPC476733
0.8791	High Similarity	NPC474704
0.8791	High Similarity	NPC475921
0.8791	High Similarity	NPC76879
0.8791	High Similarity	NPC215029
0.8778	High Similarity	NPC312215
0.8778	High Similarity	NPC167877
0.8778	High Similarity	NPC317590
0.8778	High Similarity	NPC474684
0.8778	High Similarity	NPC142361
0.8778	High Similarity	NPC96496
0.8776	High Similarity	NPC235889
0.8763	High Similarity	NPC473928
0.8763	High Similarity	NPC136289
0.875	High Similarity	NPC83709
0.8723	High Similarity	NPC48330
0.8723	High Similarity	NPC317586
0.8723	High Similarity	NPC162001
0.8723	High Similarity	NPC222845
0.8723	High Similarity	NPC470016
0.8723	High Similarity	NPC263347
0.8723	High Similarity	NPC45324
0.871	High Similarity	NPC243866
0.871	High Similarity	NPC25750
0.87	High Similarity	NPC94529
0.8696	High Similarity	NPC148414
0.8696	High Similarity	NPC175628
0.8696	High Similarity	NPC111585
0.8687	High Similarity	NPC181265
0.8687	High Similarity	NPC196528
0.8681	High Similarity	NPC183546
0.8681	High Similarity	NPC242864
0.8673	High Similarity	NPC236390
0.8667	High Similarity	NPC264127
0.8667	High Similarity	NPC31564
0.8667	High Similarity	NPC212843
0.8667	High Similarity	NPC474778
0.8667	High Similarity	NPC145879
0.8667	High Similarity	NPC195640
0.8667	High Similarity	NPC20688
0.8667	High Similarity	NPC474732
0.8667	High Similarity	NPC474970
0.8667	High Similarity	NPC51014
0.8667	High Similarity	NPC469994
0.8667	High Similarity	NPC474733
0.866	High Similarity	NPC81530
0.8646	High Similarity	NPC197386
0.8646	High Similarity	NPC153792
0.8646	High Similarity	NPC271387
0.8636	High Similarity	NPC151519
0.8632	High Similarity	NPC95565
0.8632	High Similarity	NPC477853
0.8632	High Similarity	NPC322063
0.8632	High Similarity	NPC125622
0.8632	High Similarity	NPC155676
0.8627	High Similarity	NPC43775
0.8617	High Similarity	NPC49670
0.8617	High Similarity	NPC166906
0.8614	High Similarity	NPC241927
0.8614	High Similarity	NPC258543
0.8602	High Similarity	NPC150383
0.8602	High Similarity	NPC189520
0.86	High Similarity	NPC220974
0.8587	High Similarity	NPC1015
0.8587	High Similarity	NPC32830
0.8587	High Similarity	NPC31985
0.8587	High Similarity	NPC474889
0.8587	High Similarity	NPC474245
0.8587	High Similarity	NPC186688
0.8586	High Similarity	NPC472227
0.8586	High Similarity	NPC472228
0.8586	High Similarity	NPC29705
0.8586	High Similarity	NPC137657
0.8571	High Similarity	NPC195290
0.8571	High Similarity	NPC472481
0.8571	High Similarity	NPC187376
0.8571	High Similarity	NPC159046
0.8571	High Similarity	NPC185530
0.8571	High Similarity	NPC233836
0.8571	High Similarity	NPC204450
0.8571	High Similarity	NPC58063
0.8571	High Similarity	NPC475740
0.8571	High Similarity	NPC472482
0.8571	High Similarity	NPC22388
0.8571	High Similarity	NPC472484
0.8557	High Similarity	NPC476274
0.8556	High Similarity	NPC470223
0.8556	High Similarity	NPC469948
0.8556	High Similarity	NPC323765
0.8544	High Similarity	NPC280782
0.8544	High Similarity	NPC71348
0.8542	High Similarity	NPC108078
0.8542	High Similarity	NPC190554
0.8539	High Similarity	NPC476082
0.8539	High Similarity	NPC245866
0.8539	High Similarity	NPC278648
0.8529	High Similarity	NPC197428
0.8526	High Similarity	NPC241156
0.8526	High Similarity	NPC279974
0.8523	High Similarity	NPC147066
0.8511	High Similarity	NPC109414
0.8495	Intermediate Similarity	NPC171441
0.8495	Intermediate Similarity	NPC320026
0.8495	Intermediate Similarity	NPC123854
0.8495	Intermediate Similarity	NPC44240
0.8495	Intermediate Similarity	NPC46281
0.8485	Intermediate Similarity	NPC26478
0.8478	Intermediate Similarity	NPC48866
0.8478	Intermediate Similarity	NPC247406
0.8478	Intermediate Similarity	NPC472220
0.8478	Intermediate Similarity	NPC97884
0.8478	Intermediate Similarity	NPC53911
0.8469	Intermediate Similarity	NPC476240
0.8469	Intermediate Similarity	NPC476223
0.8469	Intermediate Similarity	NPC99411
0.8469	Intermediate Similarity	NPC224720
0.8462	Intermediate Similarity	NPC73038
0.8462	Intermediate Similarity	NPC325594
0.8462	Intermediate Similarity	NPC202889
0.8462	Intermediate Similarity	NPC55309
0.8462	Intermediate Similarity	NPC28252
0.8454	Intermediate Similarity	NPC186810
0.8454	Intermediate Similarity	NPC114274
0.8454	Intermediate Similarity	NPC176845
0.8454	Intermediate Similarity	NPC166745
0.8454	Intermediate Similarity	NPC235464
0.8454	Intermediate Similarity	NPC48647
0.8447	Intermediate Similarity	NPC118860
0.8447	Intermediate Similarity	NPC231589
0.8447	Intermediate Similarity	NPC214797
0.8444	Intermediate Similarity	NPC165064
0.8444	Intermediate Similarity	NPC161423
0.8444	Intermediate Similarity	NPC227064
0.8444	Intermediate Similarity	NPC85774
0.8444	Intermediate Similarity	NPC214043
0.8444	Intermediate Similarity	NPC58841
0.8444	Intermediate Similarity	NPC100391
0.8444	Intermediate Similarity	NPC329043
0.8444	Intermediate Similarity	NPC321187
0.8438	Intermediate Similarity	NPC328162
0.8438	Intermediate Similarity	NPC49371
0.8438	Intermediate Similarity	NPC305483
0.8438	Intermediate Similarity	NPC96859
0.8438	Intermediate Similarity	NPC328371
0.8438	Intermediate Similarity	NPC120708
0.8427	Intermediate Similarity	NPC133391
0.8427	Intermediate Similarity	NPC260956
0.8421	Intermediate Similarity	NPC111015
0.8416	Intermediate Similarity	NPC59530
0.8416	Intermediate Similarity	NPC44063
0.84	Intermediate Similarity	NPC75531
0.84	Intermediate Similarity	NPC471293
0.84	Intermediate Similarity	NPC149124
0.84	Intermediate Similarity	NPC255309
0.84	Intermediate Similarity	NPC96268
0.84	Intermediate Similarity	NPC477812
0.8387	Intermediate Similarity	NPC77168

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 NPC469599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1340
0.2-0.3	3904
0.3-0.4	2531
0.4-0.5	690
0.5-0.6	182
0.6-0.7	131
0.7-0.8	151
0.8-0.85	50
0.85-0.9	24
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD6399	Phase 3
0.8864	High Similarity	NPD4786	Approved
0.8737	High Similarity	NPD6084	Phase 2
0.8737	High Similarity	NPD6083	Phase 2
0.8687	High Similarity	NPD6402	Approved
0.8687	High Similarity	NPD6675	Approved
0.8687	High Similarity	NPD5739	Approved
0.8687	High Similarity	NPD7128	Approved
0.8667	High Similarity	NPD6409	Approved
0.8667	High Similarity	NPD7521	Approved
0.8667	High Similarity	NPD7334	Approved
0.8667	High Similarity	NPD7146	Approved
0.8667	High Similarity	NPD5330	Approved
0.8667	High Similarity	NPD6684	Approved
0.8636	High Similarity	NPD3667	Approved
0.8614	High Similarity	NPD6372	Approved
0.8614	High Similarity	NPD6373	Approved
0.8515	High Similarity	NPD6881	Approved
0.8515	High Similarity	NPD6899	Approved
0.8515	High Similarity	NPD7320	Approved
0.8478	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD6903	Approved
0.8454	Intermediate Similarity	NPD5696	Approved
0.8447	Intermediate Similarity	NPD6649	Approved
0.8447	Intermediate Similarity	NPD6650	Approved
0.8444	Intermediate Similarity	NPD3665	Phase 1
0.8444	Intermediate Similarity	NPD3666	Approved
0.8444	Intermediate Similarity	NPD3133	Approved
0.8416	Intermediate Similarity	NPD5697	Approved
0.8416	Intermediate Similarity	NPD5701	Approved
0.8387	Intermediate Similarity	NPD5328	Approved
0.835	Intermediate Similarity	NPD7102	Approved
0.835	Intermediate Similarity	NPD6883	Approved
0.835	Intermediate Similarity	NPD7290	Approved
0.8333	Intermediate Similarity	NPD5695	Phase 3
0.8333	Intermediate Similarity	NPD6011	Approved
0.828	Intermediate Similarity	NPD5737	Approved
0.828	Intermediate Similarity	NPD6672	Approved
0.8269	Intermediate Similarity	NPD6847	Approved
0.8269	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8130	Phase 1
0.8269	Intermediate Similarity	NPD6869	Approved
0.8269	Intermediate Similarity	NPD6617	Approved
0.8261	Intermediate Similarity	NPD3618	Phase 1
0.8261	Intermediate Similarity	NPD6098	Approved
0.8252	Intermediate Similarity	NPD6012	Approved
0.8252	Intermediate Similarity	NPD6014	Approved
0.8252	Intermediate Similarity	NPD6013	Approved
0.8211	Intermediate Similarity	NPD6079	Approved
0.8191	Intermediate Similarity	NPD4753	Phase 2
0.8191	Intermediate Similarity	NPD6080	Approved
0.8191	Intermediate Similarity	NPD6673	Approved
0.8191	Intermediate Similarity	NPD6904	Approved
0.819	Intermediate Similarity	NPD6882	Approved
0.819	Intermediate Similarity	NPD8297	Approved
0.8163	Intermediate Similarity	NPD4755	Approved
0.8144	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6008	Approved
0.8125	Intermediate Similarity	NPD4202	Approved
0.8061	Intermediate Similarity	NPD4697	Phase 3
0.8043	Intermediate Similarity	NPD3668	Phase 3
0.8041	Intermediate Similarity	NPD7748	Approved
0.8022	Intermediate Similarity	NPD4221	Approved
0.8022	Intermediate Similarity	NPD4223	Phase 3
0.8021	Intermediate Similarity	NPD8035	Phase 2
0.8021	Intermediate Similarity	NPD8034	Phase 2
0.8021	Intermediate Similarity	NPD7515	Phase 2
0.8021	Intermediate Similarity	NPD5281	Approved
0.8021	Intermediate Similarity	NPD5284	Approved
0.8	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD4700	Approved
0.8	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD5285	Approved
0.798	Intermediate Similarity	NPD7902	Approved
0.7959	Intermediate Similarity	NPD5210	Approved
0.7959	Intermediate Similarity	NPD4629	Approved
0.7957	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD5329	Approved
0.7955	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5223	Approved
0.79	Intermediate Similarity	NPD7638	Approved
0.7895	Intermediate Similarity	NPD5208	Approved
0.7879	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5222	Approved
0.7879	Intermediate Similarity	NPD5221	Approved
0.7849	Intermediate Similarity	NPD4197	Approved
0.7843	Intermediate Similarity	NPD5226	Approved
0.7843	Intermediate Similarity	NPD5211	Phase 2
0.7843	Intermediate Similarity	NPD5224	Approved
0.7843	Intermediate Similarity	NPD5225	Approved
0.7843	Intermediate Similarity	NPD4633	Approved
0.7841	Intermediate Similarity	NPD6942	Approved
0.7841	Intermediate Similarity	NPD7339	Approved
0.7835	Intermediate Similarity	NPD5693	Phase 1
0.7835	Intermediate Similarity	NPD6050	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7818	Intermediate Similarity	NPD6335	Approved
0.78	Intermediate Similarity	NPD5173	Approved
0.7798	Intermediate Similarity	NPD6274	Approved
0.7778	Intermediate Similarity	NPD4632	Approved
0.7767	Intermediate Similarity	NPD4754	Approved
0.7767	Intermediate Similarity	NPD5175	Approved
0.7767	Intermediate Similarity	NPD5174	Approved
0.7748	Intermediate Similarity	NPD7100	Approved
0.7748	Intermediate Similarity	NPD7101	Approved
0.7742	Intermediate Similarity	NPD4788	Approved
0.7732	Intermediate Similarity	NPD5207	Approved
0.7732	Intermediate Similarity	NPD5692	Phase 3
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD6317	Approved
0.7717	Intermediate Similarity	NPD5369	Approved
0.7714	Intermediate Similarity	NPD6412	Phase 2
0.7692	Intermediate Similarity	NPD5141	Approved
0.7684	Intermediate Similarity	NPD5205	Approved
0.7684	Intermediate Similarity	NPD5279	Phase 3
0.7684	Intermediate Similarity	NPD4688	Approved
0.7684	Intermediate Similarity	NPD4689	Approved
0.7684	Intermediate Similarity	NPD4690	Approved
0.7684	Intermediate Similarity	NPD4693	Phase 3
0.7684	Intermediate Similarity	NPD4138	Approved
0.7677	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7900	Approved
0.7677	Intermediate Similarity	NPD6001	Approved
0.7658	Intermediate Similarity	NPD6314	Approved
0.7658	Intermediate Similarity	NPD6313	Approved
0.7653	Intermediate Similarity	NPD6411	Approved
0.7653	Intermediate Similarity	NPD5694	Approved
0.7636	Intermediate Similarity	NPD6868	Approved
0.7634	Intermediate Similarity	NPD6435	Approved
0.7629	Intermediate Similarity	NPD6051	Approved
0.7619	Intermediate Similarity	NPD4768	Approved
0.7619	Intermediate Similarity	NPD4767	Approved
0.7611	Intermediate Similarity	NPD6909	Approved
0.7611	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6908	Approved
0.7568	Intermediate Similarity	NPD6009	Approved
0.7553	Intermediate Similarity	NPD5362	Discontinued
0.7522	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD5786	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4694	Approved
0.7478	Intermediate Similarity	NPD7604	Phase 2
0.7477	Intermediate Similarity	NPD4729	Approved
0.7477	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD4730	Approved
0.7456	Intermediate Similarity	NPD5983	Phase 2
0.7449	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6101	Approved
0.7447	Intermediate Similarity	NPD4270	Approved
0.7447	Intermediate Similarity	NPD4269	Approved
0.7444	Intermediate Similarity	NPD3702	Approved
0.7429	Intermediate Similarity	NPD6052	Approved
0.7419	Intermediate Similarity	NPD5368	Approved
0.7419	Intermediate Similarity	NPD7525	Registered
0.7414	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5785	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6059	Approved
0.7364	Intermediate Similarity	NPD6053	Discontinued
0.7363	Intermediate Similarity	NPD6117	Approved
0.735	Intermediate Similarity	NPD6336	Discontinued
0.735	Intermediate Similarity	NPD6616	Approved
0.734	Intermediate Similarity	NPD4692	Approved
0.734	Intermediate Similarity	NPD4139	Approved
0.7339	Intermediate Similarity	NPD5135	Approved
0.7339	Intermediate Similarity	NPD5251	Approved
0.7339	Intermediate Similarity	NPD5249	Phase 3
0.7339	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5250	Approved
0.7339	Intermediate Similarity	NPD5169	Approved
0.7339	Intermediate Similarity	NPD4634	Approved
0.7339	Intermediate Similarity	NPD5247	Approved
0.7339	Intermediate Similarity	NPD5248	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4785	Approved
0.7333	Intermediate Similarity	NPD4784	Approved
0.7312	Intermediate Similarity	NPD4195	Approved
0.7303	Intermediate Similarity	NPD5777	Approved
0.7303	Intermediate Similarity	NPD4243	Approved
0.73	Intermediate Similarity	NPD7637	Suspended
0.7288	Intermediate Similarity	NPD7078	Approved
0.7288	Intermediate Similarity	NPD8293	Discontinued
0.7283	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5215	Approved
0.7273	Intermediate Similarity	NPD5127	Approved
0.7273	Intermediate Similarity	NPD5216	Approved
0.7255	Intermediate Similarity	NPD5654	Approved
0.7245	Intermediate Similarity	NPD3573	Approved
0.7245	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6370	Approved
0.7234	Intermediate Similarity	NPD4252	Approved
0.7234	Intermediate Similarity	NPD4695	Discontinued
0.7227	Intermediate Similarity	NPD7736	Approved
0.7222	Intermediate Similarity	NPD6614	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