NPASS Compound

Structure

NPC114274 OpenBabel07101719512D 27 30 0 0 1 0 0 0 0 0999 V2000 -0.5909 -2.0032 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 -1.5388 0.5000 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 4.3301 1.5000 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 3.4641 3.0000 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 -1.2601 -1.2601 0.0000 C 0 0 1 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 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 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 1 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -0.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 1 1 6 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 23 2 0 0 0 0 14 22 1 1 0 0 0 15 19 1 0 0 0 0 15 22 1 1 0 0 0 16 19 1 0 0 0 0 16 21 1 1 0 0 0 17 19 1 0 0 0 0 17 24 1 6 0 0 0 18 22 1 6 0 0 0 18 25 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	2.151
LogD:	1.795
LogS:	-2.768
# Rotatable Bonds:	2
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	4.926
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.541
MDCK Permeability:	2.5854444174910896e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.505
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.79
Plasma Protein Binding (PPB):	76.65483856201172%
Volume Distribution (VD):	0.282
Pgp-substrate:	23.01580238342285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.435
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	10.842
Half-life (T1/2):	0.93

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.349
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.359
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.578
Carcinogencity:	0.815
Eye Corrosion:	0.006
Eye Irritation:	0.021
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC114274

Natural Product ID:	NPC114274
*Common Name:**	Rel-Bendigole D
IUPAC Name:	(2S)-2-[(7R,8R,9S,10R,12S,13S,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]propanoic acid
Synonyms:	Rel-Bendigole D
Standard InCHIKey:	RIPUUOOMDLZCBV-QYVBNZPWSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-11(20(26)27)14-4-5-15-19-16(10-18(25)22(14,15)3)21(2)7-6-13(23)8-12(21)9-17(19)24/h6-8,11,14-19,24-25H,4-5,9-10H2,1-3H3,(H,26,27)/t11-,14+,15-,16-,17+,18-,19-,21-,22+/m0/s1
SMILES:	C[C@@H]([C@H]1CC[C@H]2[C@H]3[C@H](C[C@@H]([C@]12C)O)[C@@]1(C)C=CC(=O)C=C1C[C@H]3O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915269
PubChem CID:	54764154
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:0000516] Dihydroxy 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
NPO33346	Actinomadura sp. SBMs009	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21684166]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	30000.0	nM	PMID[502212]

☑ 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 NPC114274 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	189
0.1-0.2	1086
0.2-0.3	4236
0.3-0.4	9098
0.4-0.5	12321
0.5-0.6	6266
0.6-0.7	5631
0.7-0.8	3188
0.8-0.85	553
0.85-0.9	118
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC108078
0.9149	High Similarity	NPC477853
0.914	High Similarity	NPC166906
0.9043	High Similarity	NPC317586
0.9043	High Similarity	NPC470016
0.9032	High Similarity	NPC477855
0.9011	High Similarity	NPC328539
0.901	High Similarity	NPC197428
0.8958	High Similarity	NPC477854
0.8947	High Similarity	NPC173272
0.8947	High Similarity	NPC96859
0.8947	High Similarity	NPC328162
0.8947	High Similarity	NPC305483
0.8936	High Similarity	NPC196485
0.8936	High Similarity	NPC245972
0.8925	High Similarity	NPC168027
0.8925	High Similarity	NPC185936
0.8913	High Similarity	NPC186688
0.89	High Similarity	NPC472925
0.8854	High Similarity	NPC320306
0.8842	High Similarity	NPC48330
0.8835	High Similarity	NPC71348
0.8788	High Similarity	NPC312900
0.8776	High Similarity	NPC472924
0.8776	High Similarity	NPC81530
0.8737	High Similarity	NPC471207
0.8737	High Similarity	NPC111015
0.8723	High Similarity	NPC211403
0.8723	High Similarity	NPC272746
0.8723	High Similarity	NPC198242
0.8723	High Similarity	NPC131872
0.8713	High Similarity	NPC44063
0.871	High Similarity	NPC474704
0.871	High Similarity	NPC275740
0.871	High Similarity	NPC119416
0.871	High Similarity	NPC1015
0.871	High Similarity	NPC86319
0.871	High Similarity	NPC31985
0.871	High Similarity	NPC475921
0.87	High Similarity	NPC255309
0.8696	High Similarity	NPC475740
0.8696	High Similarity	NPC58063
0.8696	High Similarity	NPC142361
0.8696	High Similarity	NPC474684
0.8687	High Similarity	NPC136289
0.8687	High Similarity	NPC293753
0.8673	High Similarity	NPC327431
0.8673	High Similarity	NPC316964
0.8673	High Similarity	NPC144956
0.866	High Similarity	NPC43747
0.866	High Similarity	NPC190554
0.8646	High Similarity	NPC469995
0.8646	High Similarity	NPC318282
0.8646	High Similarity	NPC173875
0.8646	High Similarity	NPC174948
0.8641	High Similarity	NPC5284
0.8632	High Similarity	NPC206810
0.8632	High Similarity	NPC79117
0.8614	High Similarity	NPC96377
0.8614	High Similarity	NPC231530
0.8614	High Similarity	NPC323834
0.8614	High Similarity	NPC278628
0.8602	High Similarity	NPC143767
0.8602	High Similarity	NPC242864
0.8602	High Similarity	NPC471722
0.8602	High Similarity	NPC131470
0.86	High Similarity	NPC159442
0.86	High Similarity	NPC264048
0.8587	High Similarity	NPC474733
0.8587	High Similarity	NPC31564
0.8587	High Similarity	NPC155011
0.8587	High Similarity	NPC474732
0.8587	High Similarity	NPC145879
0.8587	High Similarity	NPC474778
0.8586	High Similarity	NPC476223
0.8586	High Similarity	NPC476240
0.8586	High Similarity	NPC224720
0.8585	High Similarity	NPC270958
0.8571	High Similarity	NPC197386
0.8571	High Similarity	NPC103051
0.8558	High Similarity	NPC472928
0.8557	High Similarity	NPC249954
0.8557	High Similarity	NPC58052
0.8557	High Similarity	NPC111684
0.8557	High Similarity	NPC95565
0.8557	High Similarity	NPC301534
0.8557	High Similarity	NPC192428
0.8557	High Similarity	NPC250757
0.8557	High Similarity	NPC328371
0.8544	High Similarity	NPC2766
0.8544	High Similarity	NPC241927
0.8544	High Similarity	NPC258543
0.8542	High Similarity	NPC470385
0.8542	High Similarity	NPC470386
0.8542	High Similarity	NPC279410
0.8542	High Similarity	NPC119562
0.8529	High Similarity	NPC475294
0.8526	High Similarity	NPC189520
0.8526	High Similarity	NPC86266
0.8526	High Similarity	NPC212301
0.8526	High Similarity	NPC110657
0.8515	High Similarity	NPC235889
0.8515	High Similarity	NPC96268
0.8511	High Similarity	NPC128496
0.85	High Similarity	NPC22388
0.85	High Similarity	NPC234892
0.8495	Intermediate Similarity	NPC159046
0.8495	Intermediate Similarity	NPC153604
0.8495	Intermediate Similarity	NPC233836
0.8495	Intermediate Similarity	NPC187376
0.8495	Intermediate Similarity	NPC298904
0.8485	Intermediate Similarity	NPC287833
0.8485	Intermediate Similarity	NPC476274
0.8485	Intermediate Similarity	NPC472972
0.8485	Intermediate Similarity	NPC15390
0.8478	Intermediate Similarity	NPC469948
0.8478	Intermediate Similarity	NPC29447
0.8478	Intermediate Similarity	NPC470574
0.8476	Intermediate Similarity	NPC234042
0.8476	Intermediate Similarity	NPC152117
0.8469	Intermediate Similarity	NPC253826
0.8469	Intermediate Similarity	NPC18509
0.8469	Intermediate Similarity	NPC99726
0.8469	Intermediate Similarity	NPC226986
0.8469	Intermediate Similarity	NPC292133
0.8462	Intermediate Similarity	NPC239097
0.8454	Intermediate Similarity	NPC200702
0.8454	Intermediate Similarity	NPC271195
0.8454	Intermediate Similarity	NPC279974
0.8454	Intermediate Similarity	NPC259286
0.8454	Intermediate Similarity	NPC473240
0.8454	Intermediate Similarity	NPC88310
0.8454	Intermediate Similarity	NPC139570
0.8454	Intermediate Similarity	NPC473170
0.8454	Intermediate Similarity	NPC255809
0.8454	Intermediate Similarity	NPC470232
0.8454	Intermediate Similarity	NPC469599
0.8454	Intermediate Similarity	NPC98639
0.8447	Intermediate Similarity	NPC469844
0.8447	Intermediate Similarity	NPC295244
0.8447	Intermediate Similarity	NPC94529
0.8438	Intermediate Similarity	NPC470376
0.8438	Intermediate Similarity	NPC107674
0.8438	Intermediate Similarity	NPC470375
0.8438	Intermediate Similarity	NPC224060
0.8438	Intermediate Similarity	NPC69454
0.8438	Intermediate Similarity	NPC475255
0.8438	Intermediate Similarity	NPC170220
0.8438	Intermediate Similarity	NPC134826
0.8438	Intermediate Similarity	NPC244356
0.8438	Intermediate Similarity	NPC141497
0.8431	Intermediate Similarity	NPC149047
0.8431	Intermediate Similarity	NPC181265
0.8431	Intermediate Similarity	NPC102352
0.8426	Intermediate Similarity	NPC118638
0.8421	Intermediate Similarity	NPC85173
0.8421	Intermediate Similarity	NPC80401
0.8421	Intermediate Similarity	NPC471896
0.8421	Intermediate Similarity	NPC191684
0.8421	Intermediate Similarity	NPC183283
0.8421	Intermediate Similarity	NPC126993
0.8421	Intermediate Similarity	NPC48010
0.8416	Intermediate Similarity	NPC275583
0.8416	Intermediate Similarity	NPC282233
0.8416	Intermediate Similarity	NPC247957
0.8416	Intermediate Similarity	NPC249187
0.8416	Intermediate Similarity	NPC95585
0.8416	Intermediate Similarity	NPC55872
0.8416	Intermediate Similarity	NPC140723
0.8416	Intermediate Similarity	NPC251017
0.8404	Intermediate Similarity	NPC193360
0.8404	Intermediate Similarity	NPC474677
0.8404	Intermediate Similarity	NPC473229
0.8404	Intermediate Similarity	NPC53911
0.8404	Intermediate Similarity	NPC158778
0.84	Intermediate Similarity	NPC302537
0.84	Intermediate Similarity	NPC163372
0.8396	Intermediate Similarity	NPC255017
0.8396	Intermediate Similarity	NPC202889
0.8396	Intermediate Similarity	NPC472926
0.8387	Intermediate Similarity	NPC118648
0.8387	Intermediate Similarity	NPC28252
0.8387	Intermediate Similarity	NPC475022
0.8387	Intermediate Similarity	NPC55309
0.8387	Intermediate Similarity	NPC72133
0.8387	Intermediate Similarity	NPC222613
0.8384	Intermediate Similarity	NPC471717
0.8384	Intermediate Similarity	NPC108368
0.8384	Intermediate Similarity	NPC194196
0.8384	Intermediate Similarity	NPC57079
0.8381	Intermediate Similarity	NPC118860
0.8381	Intermediate Similarity	NPC231589
0.8381	Intermediate Similarity	NPC214797
0.837	Intermediate Similarity	NPC214043
0.837	Intermediate Similarity	NPC59453
0.837	Intermediate Similarity	NPC33913
0.837	Intermediate Similarity	NPC472265
0.837	Intermediate Similarity	NPC221758
0.837	Intermediate Similarity	NPC85774
0.8367	Intermediate Similarity	NPC7124

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 NPC114274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1358
0.2-0.3	3742
0.3-0.4	2533
0.4-0.5	821
0.5-0.6	187
0.6-0.7	154
0.7-0.8	120
0.8-0.85	39
0.85-0.9	36
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD6079	Approved
0.8947	High Similarity	NPD5222	Approved
0.8947	High Similarity	NPD5220	Clinical (unspecified phase)
0.8947	High Similarity	NPD5221	Approved
0.8913	High Similarity	NPD5328	Approved
0.8854	High Similarity	NPD5173	Approved
0.8713	High Similarity	NPD5697	Approved
0.8673	High Similarity	NPD4696	Approved
0.8673	High Similarity	NPD5286	Approved
0.8673	High Similarity	NPD5285	Approved
0.8627	High Similarity	NPD6011	Approved
0.8627	High Similarity	NPD6881	Approved
0.8627	High Similarity	NPD6899	Approved
0.8587	High Similarity	NPD3618	Phase 1
0.8586	High Similarity	NPD5223	Approved
0.8571	High Similarity	NPD4632	Approved
0.8557	High Similarity	NPD4697	Phase 3
0.8544	High Similarity	NPD6012	Approved
0.8544	High Similarity	NPD6013	Approved
0.8544	High Similarity	NPD6014	Approved
0.85	High Similarity	NPD4633	Approved
0.85	High Similarity	NPD5225	Approved
0.85	High Similarity	NPD5224	Approved
0.85	High Similarity	NPD5226	Approved
0.85	High Similarity	NPD5211	Phase 2
0.8469	Intermediate Similarity	NPD4755	Approved
0.8462	Intermediate Similarity	NPD7290	Approved
0.8462	Intermediate Similarity	NPD7102	Approved
0.8462	Intermediate Similarity	NPD6883	Approved
0.8431	Intermediate Similarity	NPD6402	Approved
0.8431	Intermediate Similarity	NPD7128	Approved
0.8431	Intermediate Similarity	NPD6675	Approved
0.8431	Intermediate Similarity	NPD5739	Approved
0.8416	Intermediate Similarity	NPD5175	Approved
0.8416	Intermediate Similarity	NPD5174	Approved
0.8381	Intermediate Similarity	NPD6617	Approved
0.8381	Intermediate Similarity	NPD8130	Phase 1
0.8381	Intermediate Similarity	NPD6847	Approved
0.8381	Intermediate Similarity	NPD6869	Approved
0.8381	Intermediate Similarity	NPD6649	Approved
0.8381	Intermediate Similarity	NPD6650	Approved
0.837	Intermediate Similarity	NPD4786	Approved
0.8352	Intermediate Similarity	NPD3667	Approved
0.835	Intermediate Similarity	NPD5701	Approved
0.8333	Intermediate Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD6009	Approved
0.8333	Intermediate Similarity	NPD5141	Approved
0.8302	Intermediate Similarity	NPD8297	Approved
0.8302	Intermediate Similarity	NPD6882	Approved
0.83	Intermediate Similarity	NPD4700	Approved
0.8286	Intermediate Similarity	NPD4634	Approved
0.8269	Intermediate Similarity	NPD7320	Approved
0.8252	Intermediate Similarity	NPD6008	Approved
0.8247	Intermediate Similarity	NPD4202	Approved
0.8247	Intermediate Similarity	NPD6399	Phase 3
0.819	Intermediate Similarity	NPD6373	Approved
0.819	Intermediate Similarity	NPD6372	Approved
0.8172	Intermediate Similarity	NPD3666	Approved
0.8172	Intermediate Similarity	NPD3133	Approved
0.8172	Intermediate Similarity	NPD3665	Phase 1
0.8108	Intermediate Similarity	NPD6319	Approved
0.8095	Intermediate Similarity	NPD5168	Approved
0.8095	Intermediate Similarity	NPD4730	Approved
0.8095	Intermediate Similarity	NPD4729	Approved
0.8073	Intermediate Similarity	NPD6868	Approved
0.8058	Intermediate Similarity	NPD4754	Approved
0.8037	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5983	Phase 2
0.802	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD6317	Approved
0.798	Intermediate Similarity	NPD7748	Approved
0.7944	Intermediate Similarity	NPD5250	Approved
0.7944	Intermediate Similarity	NPD5169	Approved
0.7944	Intermediate Similarity	NPD5251	Approved
0.7944	Intermediate Similarity	NPD5247	Approved
0.7944	Intermediate Similarity	NPD5249	Phase 3
0.7944	Intermediate Similarity	NPD5135	Approved
0.7944	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD5248	Approved
0.7941	Intermediate Similarity	NPD7640	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.7938	Intermediate Similarity	NPD4753	Phase 2
0.7928	Intermediate Similarity	NPD6335	Approved
0.7928	Intermediate Similarity	NPD6313	Approved
0.7928	Intermediate Similarity	NPD6314	Approved
0.7925	Intermediate Similarity	NPD5128	Approved
0.7921	Intermediate Similarity	NPD6084	Phase 2
0.7921	Intermediate Similarity	NPD6083	Phase 2
0.7917	Intermediate Similarity	NPD3573	Approved
0.7909	Intermediate Similarity	NPD6274	Approved
0.7905	Intermediate Similarity	NPD4768	Approved
0.7905	Intermediate Similarity	NPD4767	Approved
0.79	Intermediate Similarity	NPD4629	Approved
0.79	Intermediate Similarity	NPD5210	Approved
0.7895	Intermediate Similarity	NPD7604	Phase 2
0.7895	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5215	Approved
0.787	Intermediate Similarity	NPD5217	Approved
0.787	Intermediate Similarity	NPD5127	Approved
0.787	Intermediate Similarity	NPD5216	Approved
0.7857	Intermediate Similarity	NPD7101	Approved
0.7857	Intermediate Similarity	NPD7100	Approved
0.7838	Intermediate Similarity	NPD7115	Discovery
0.7835	Intermediate Similarity	NPD6672	Approved
0.7835	Intermediate Similarity	NPD5737	Approved
0.7826	Intermediate Similarity	NPD7492	Approved
0.7812	Intermediate Similarity	NPD6409	Approved
0.7812	Intermediate Similarity	NPD7146	Approved
0.7812	Intermediate Similarity	NPD5330	Approved
0.7812	Intermediate Similarity	NPD6684	Approved
0.7812	Intermediate Similarity	NPD5279	Phase 3
0.7812	Intermediate Similarity	NPD7521	Approved
0.7812	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD3668	Phase 3
0.7788	Intermediate Similarity	NPD6054	Approved
0.7778	Intermediate Similarity	NPD5281	Approved
0.7778	Intermediate Similarity	NPD5284	Approved
0.7766	Intermediate Similarity	NPD4221	Approved
0.7766	Intermediate Similarity	NPD4223	Phase 3
0.7759	Intermediate Similarity	NPD6336	Discontinued
0.7759	Intermediate Similarity	NPD6616	Approved
0.7745	Intermediate Similarity	NPD7902	Approved
0.7723	Intermediate Similarity	NPD5695	Phase 3
0.7719	Intermediate Similarity	NPD6016	Approved
0.7719	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6015	Approved
0.7692	Intermediate Similarity	NPD7078	Approved
0.767	Intermediate Similarity	NPD5696	Approved
0.7658	Intermediate Similarity	NPD5167	Approved
0.7653	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD6903	Approved
0.7652	Intermediate Similarity	NPD5988	Approved
0.7652	Intermediate Similarity	NPD6370	Approved
0.7629	Intermediate Similarity	NPD5690	Phase 2
0.7627	Intermediate Similarity	NPD7736	Approved
0.7604	Intermediate Similarity	NPD4197	Approved
0.7553	Intermediate Similarity	NPD4695	Discontinued
0.7549	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6697	Approved
0.7527	Intermediate Similarity	NPD6118	Approved
0.7527	Intermediate Similarity	NPD6115	Approved
0.7527	Intermediate Similarity	NPD6114	Approved
0.7526	Intermediate Similarity	NPD5329	Approved
0.7478	Intermediate Similarity	NPD6059	Approved
0.7451	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7900	Approved
0.7449	Intermediate Similarity	NPD4690	Approved
0.7449	Intermediate Similarity	NPD4688	Approved
0.7449	Intermediate Similarity	NPD5205	Approved
0.7449	Intermediate Similarity	NPD4138	Approved
0.7449	Intermediate Similarity	NPD4693	Phase 3
0.7449	Intermediate Similarity	NPD4689	Approved
0.7447	Intermediate Similarity	NPD4195	Approved
0.7426	Intermediate Similarity	NPD6411	Approved
0.7426	Intermediate Similarity	NPD8035	Phase 2
0.7426	Intermediate Similarity	NPD8034	Phase 2
0.7414	Intermediate Similarity	NPD6909	Approved
0.7414	Intermediate Similarity	NPD6908	Approved
0.74	Intermediate Similarity	NPD6904	Approved
0.74	Intermediate Similarity	NPD6080	Approved
0.74	Intermediate Similarity	NPD6673	Approved
0.7395	Intermediate Similarity	NPD8293	Discontinued
0.7391	Intermediate Similarity	NPD3703	Phase 2
0.7391	Intermediate Similarity	NPD6942	Approved
0.7391	Intermediate Similarity	NPD7339	Approved
0.7368	Intermediate Similarity	NPD7525	Registered
0.734	Intermediate Similarity	NPD3617	Approved
0.7339	Intermediate Similarity	NPD6412	Phase 2
0.732	Intermediate Similarity	NPD4788	Approved
0.7312	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6117	Approved
0.73	Intermediate Similarity	NPD5208	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD6001	Approved
0.7273	Intermediate Similarity	NPD5280	Approved
0.7273	Intermediate Similarity	NPD4694	Approved
0.7255	Intermediate Similarity	NPD5694	Approved
0.7255	Intermediate Similarity	NPD5693	Phase 1
0.7234	Intermediate Similarity	NPD6116	Phase 1
0.7228	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6101	Approved
0.7228	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5779	Approved
0.7184	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD1694	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.717	Intermediate Similarity	NPD5290	Discontinued
0.7168	Intermediate Similarity	NPD6053	Discontinued
0.7167	Intermediate Similarity	NPD7507	Approved
0.7158	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5692	Phase 3
0.7157	Intermediate Similarity	NPD5207	Approved
0.7143	Intermediate Similarity	NPD4747	Approved
0.7143	Intermediate Similarity	NPD4691	Approved
0.71	Intermediate Similarity	NPD6098	Approved
0.71	Intermediate Similarity	NPD4623	Approved
0.71	Intermediate Similarity	NPD4519	Discontinued
0.7097	Intermediate Similarity	NPD4058	Approved
0.7097	Intermediate Similarity	NPD6113	Clinical (unspecified phase)

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