NPASS Compound

Structure

NPC108078 OpenBabel07101719142D 29 32 0 0 1 0 0 0 0 0999 V2000 -2.2382 -1.4680 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 -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 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 0.3872 -1.7953 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 2 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 1.0563 -2.5385 0.0000 C 0 0 0 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 2.5981 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 0.7473 -3.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0345 -2.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 1 1 1 0 0 0 13 16 1 0 0 0 0 14 23 1 0 0 0 0 15 25 2 0 0 0 0 16 24 1 1 0 0 0 17 22 1 0 0 0 0 17 24 1 1 0 0 0 18 22 1 0 0 0 0 18 23 1 1 0 0 0 19 22 1 0 0 0 0 19 26 1 6 0 0 0 20 24 1 6 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.24
Volume:	422.84
LogP:	2.771
LogD:	2.687
LogS:	-3.323
# Rotatable Bonds:	4
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	4.797
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.409
MDCK Permeability:	1.9089797206106596e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.497
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.816
Plasma Protein Binding (PPB):	87.47692108154297%
Volume Distribution (VD):	0.312
Pgp-substrate:	17.35222625732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.459
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.257
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	8.122
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.185
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.81
Carcinogencity:	0.595
Eye Corrosion:	0.012
Eye Irritation:	0.045
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC108078

Natural Product ID:	NPC108078
*Common Name:**	Rel-Bendigole F
IUPAC Name:	(4R)-4-[(7R,8R,9S,10R,12S,13R,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]pentanoic acid
Synonyms:	Rel-Bendigole F
Standard InCHIKey:	QKYFOPPSEWXMGR-DFQOQHGMSA-N
Standard InCHI:	InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h8-10,13,16-20,22,26-27H,4-7,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
SMILES:	C[C@H](CCC(=O)O)[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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915271
PubChem CID:	5283999
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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	71000.0	nM	PMID[521158]

☑ 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 NPC108078 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	181
0.1-0.2	1036
0.2-0.3	4109
0.3-0.4	9880
0.4-0.5	11673
0.5-0.6	6067
0.6-0.7	5709
0.7-0.8	3366
0.8-0.85	537
0.85-0.9	123
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC114274
0.9239	High Similarity	NPC245972
0.9239	High Similarity	NPC196485
0.9149	High Similarity	NPC320306
0.9032	High Similarity	NPC111015
0.9032	High Similarity	NPC166906
0.9022	High Similarity	NPC272746
0.9011	High Similarity	NPC474704
0.9011	High Similarity	NPC475921
0.9011	High Similarity	NPC1015
0.9011	High Similarity	NPC186688
0.9011	High Similarity	NPC31985
0.9	High Similarity	NPC58063
0.9	High Similarity	NPC142361
0.9	High Similarity	NPC474684
0.9	High Similarity	NPC475740
0.8969	High Similarity	NPC293753
0.8958	High Similarity	NPC327431
0.8936	High Similarity	NPC317586
0.8936	High Similarity	NPC470016
0.8911	High Similarity	NPC197428
0.8901	High Similarity	NPC471722
0.8901	High Similarity	NPC242864
0.8889	High Similarity	NPC31564
0.8889	High Similarity	NPC155011
0.8889	High Similarity	NPC474778
0.8889	High Similarity	NPC474733
0.8889	High Similarity	NPC474732
0.8889	High Similarity	NPC145879
0.8854	High Similarity	NPC477854
0.8854	High Similarity	NPC103051
0.8842	High Similarity	NPC305483
0.8842	High Similarity	NPC250757
0.8842	High Similarity	NPC96859
0.8842	High Similarity	NPC173272
0.8842	High Similarity	NPC328162
0.8842	High Similarity	NPC477853
0.8842	High Similarity	NPC301534
0.883	High Similarity	NPC279410
0.883	High Similarity	NPC119562
0.8817	High Similarity	NPC189520
0.8817	High Similarity	NPC86266
0.8817	High Similarity	NPC110657
0.8817	High Similarity	NPC131872
0.8817	High Similarity	NPC212301
0.8804	High Similarity	NPC119416
0.8804	High Similarity	NPC128496
0.88	High Similarity	NPC472925
0.8791	High Similarity	NPC187376
0.8791	High Similarity	NPC159046
0.8791	High Similarity	NPC233836
0.8778	High Similarity	NPC29447
0.8778	High Similarity	NPC470574
0.8776	High Similarity	NPC234892
0.8776	High Similarity	NPC22388
0.875	High Similarity	NPC253826
0.875	High Similarity	NPC99726
0.8738	High Similarity	NPC71348
0.8737	High Similarity	NPC88310
0.8737	High Similarity	NPC48330
0.8737	High Similarity	NPC271195
0.8737	High Similarity	NPC279974
0.8723	High Similarity	NPC107674
0.8723	High Similarity	NPC141497
0.8723	High Similarity	NPC170220
0.8723	High Similarity	NPC477855
0.8723	High Similarity	NPC475255
0.8723	High Similarity	NPC470376
0.8723	High Similarity	NPC470375
0.871	High Similarity	NPC85173
0.871	High Similarity	NPC126993
0.871	High Similarity	NPC471896
0.871	High Similarity	NPC48010
0.871	High Similarity	NPC191684
0.8696	High Similarity	NPC328539
0.8696	High Similarity	NPC193360
0.8687	High Similarity	NPC249187
0.8687	High Similarity	NPC247957
0.8687	High Similarity	NPC312900
0.8681	High Similarity	NPC475022
0.8681	High Similarity	NPC55309
0.8681	High Similarity	NPC222613
0.8681	High Similarity	NPC28252
0.8681	High Similarity	NPC72133
0.8681	High Similarity	NPC118648
0.8673	High Similarity	NPC472924
0.8667	High Similarity	NPC221758
0.8667	High Similarity	NPC472265
0.8667	High Similarity	NPC214043
0.8667	High Similarity	NPC85774
0.8667	High Similarity	NPC59453
0.8667	High Similarity	NPC33913
0.866	High Similarity	NPC108368
0.866	High Similarity	NPC57079
0.866	High Similarity	NPC194196
0.8646	High Similarity	NPC471153
0.8646	High Similarity	NPC472941
0.8646	High Similarity	NPC456
0.8646	High Similarity	NPC7124
0.8632	High Similarity	NPC49670
0.8632	High Similarity	NPC8993
0.8632	High Similarity	NPC471207
0.8617	High Similarity	NPC185936
0.8617	High Similarity	NPC4036
0.8617	High Similarity	NPC233455
0.8617	High Similarity	NPC145067
0.8617	High Similarity	NPC26888
0.8617	High Similarity	NPC168027
0.8617	High Similarity	NPC233116
0.8617	High Similarity	NPC65120
0.8617	High Similarity	NPC297265
0.8617	High Similarity	NPC475806
0.8617	High Similarity	NPC473998
0.8617	High Similarity	NPC158030
0.8602	High Similarity	NPC275740
0.8602	High Similarity	NPC146554
0.8602	High Similarity	NPC262043
0.8602	High Similarity	NPC77168
0.8602	High Similarity	NPC473999
0.8602	High Similarity	NPC26959
0.8602	High Similarity	NPC309603
0.8602	High Similarity	NPC262858
0.8602	High Similarity	NPC472240
0.8602	High Similarity	NPC84271
0.8602	High Similarity	NPC102414
0.8602	High Similarity	NPC268406
0.8602	High Similarity	NPC32830
0.8602	High Similarity	NPC474245
0.8602	High Similarity	NPC86319
0.86	High Similarity	NPC255309
0.8587	High Similarity	NPC93778
0.8587	High Similarity	NPC141292
0.8587	High Similarity	NPC96496
0.8586	High Similarity	NPC136289
0.8586	High Similarity	NPC477054
0.8571	High Similarity	NPC266955
0.8571	High Similarity	NPC154072
0.8571	High Similarity	NPC470074
0.8571	High Similarity	NPC469948
0.8571	High Similarity	NPC316964
0.8571	High Similarity	NPC197823
0.8557	High Similarity	NPC122294
0.8557	High Similarity	NPC43747
0.8557	High Similarity	NPC190554
0.8544	High Similarity	NPC5284
0.8542	High Similarity	NPC174948
0.8542	High Similarity	NPC469995
0.8542	High Similarity	NPC318282
0.8542	High Similarity	NPC469599
0.8542	High Similarity	NPC173875
0.8542	High Similarity	NPC476174
0.8526	High Similarity	NPC206810
0.8526	High Similarity	NPC134826
0.8526	High Similarity	NPC12722
0.8526	High Similarity	NPC470224
0.8526	High Similarity	NPC79117
0.8526	High Similarity	NPC214756
0.8526	High Similarity	NPC474736
0.8526	High Similarity	NPC295643
0.8526	High Similarity	NPC272075
0.8515	High Similarity	NPC278628
0.8515	High Similarity	NPC257353
0.8515	High Similarity	NPC323834
0.8515	High Similarity	NPC96377
0.8515	High Similarity	NPC231530
0.8511	High Similarity	NPC475965
0.8511	High Similarity	NPC175628
0.8511	High Similarity	NPC469400
0.8511	High Similarity	NPC474842
0.8511	High Similarity	NPC148414
0.8511	High Similarity	NPC111585
0.85	High Similarity	NPC264048
0.85	High Similarity	NPC95899
0.8495	Intermediate Similarity	NPC310752
0.8495	Intermediate Similarity	NPC471724
0.8495	Intermediate Similarity	NPC143767
0.8495	Intermediate Similarity	NPC474677
0.8495	Intermediate Similarity	NPC131470
0.8495	Intermediate Similarity	NPC473229
0.8495	Intermediate Similarity	NPC292491
0.8491	Intermediate Similarity	NPC270958
0.8485	Intermediate Similarity	NPC477053
0.8485	Intermediate Similarity	NPC282524
0.8485	Intermediate Similarity	NPC115899
0.8485	Intermediate Similarity	NPC476223
0.8485	Intermediate Similarity	NPC81530
0.8485	Intermediate Similarity	NPC477052
0.8485	Intermediate Similarity	NPC476240
0.8485	Intermediate Similarity	NPC477051
0.8485	Intermediate Similarity	NPC224720
0.8478	Intermediate Similarity	NPC51014
0.8478	Intermediate Similarity	NPC474970
0.8478	Intermediate Similarity	NPC73038
0.8469	Intermediate Similarity	NPC166745
0.8469	Intermediate Similarity	NPC478056
0.8469	Intermediate Similarity	NPC235464
0.8469	Intermediate Similarity	NPC197386
0.8469	Intermediate Similarity	NPC119036
0.8469	Intermediate Similarity	NPC16021
0.8462	Intermediate Similarity	NPC473246

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 NPC108078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1302
0.2-0.3	3688
0.3-0.4	2645
0.4-0.5	799
0.5-0.6	218
0.6-0.7	135
0.7-0.8	132
0.8-0.85	64
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9022	High Similarity	NPD6079	Approved
0.8804	High Similarity	NPD5328	Approved
0.8681	High Similarity	NPD3618	Phase 1
0.8667	High Similarity	NPD4786	Approved
0.8646	High Similarity	NPD5221	Approved
0.8646	High Similarity	NPD5222	Approved
0.8646	High Similarity	NPD5220	Clinical (unspecified phase)
0.8617	High Similarity	NPD7515	Phase 2
0.8557	High Similarity	NPD5173	Approved
0.8529	High Similarity	NPD6899	Approved
0.8529	High Similarity	NPD6881	Approved
0.8526	High Similarity	NPD6399	Phase 3
0.8444	Intermediate Similarity	NPD3667	Approved
0.8431	Intermediate Similarity	NPD5697	Approved
0.8384	Intermediate Similarity	NPD5286	Approved
0.8384	Intermediate Similarity	NPD4696	Approved
0.8384	Intermediate Similarity	NPD5285	Approved
0.8365	Intermediate Similarity	NPD6883	Approved
0.8365	Intermediate Similarity	NPD7290	Approved
0.8365	Intermediate Similarity	NPD7102	Approved
0.835	Intermediate Similarity	NPD6011	Approved
0.8333	Intermediate Similarity	NPD6402	Approved
0.8333	Intermediate Similarity	NPD7128	Approved
0.8333	Intermediate Similarity	NPD4202	Approved
0.8333	Intermediate Similarity	NPD6675	Approved
0.8333	Intermediate Similarity	NPD5739	Approved
0.8302	Intermediate Similarity	NPD4632	Approved
0.83	Intermediate Similarity	NPD5223	Approved
0.8286	Intermediate Similarity	NPD6650	Approved
0.8286	Intermediate Similarity	NPD8130	Phase 1
0.8286	Intermediate Similarity	NPD6617	Approved
0.8286	Intermediate Similarity	NPD6847	Approved
0.8286	Intermediate Similarity	NPD6869	Approved
0.8286	Intermediate Similarity	NPD6649	Approved
0.8283	Intermediate Similarity	NPD7638	Approved
0.8269	Intermediate Similarity	NPD6012	Approved
0.8269	Intermediate Similarity	NPD6014	Approved
0.8269	Intermediate Similarity	NPD6013	Approved
0.8265	Intermediate Similarity	NPD4697	Phase 3
0.8261	Intermediate Similarity	NPD3133	Approved
0.8261	Intermediate Similarity	NPD3665	Phase 1
0.8261	Intermediate Similarity	NPD3666	Approved
0.8247	Intermediate Similarity	NPD7748	Approved
0.8218	Intermediate Similarity	NPD5224	Approved
0.8218	Intermediate Similarity	NPD5226	Approved
0.8218	Intermediate Similarity	NPD4633	Approved
0.8218	Intermediate Similarity	NPD5225	Approved
0.8218	Intermediate Similarity	NPD5211	Phase 2
0.8208	Intermediate Similarity	NPD8297	Approved
0.8208	Intermediate Similarity	NPD6882	Approved
0.82	Intermediate Similarity	NPD7639	Approved
0.82	Intermediate Similarity	NPD7640	Approved
0.8182	Intermediate Similarity	NPD6084	Phase 2
0.8182	Intermediate Similarity	NPD6083	Phase 2
0.8182	Intermediate Similarity	NPD4755	Approved
0.8173	Intermediate Similarity	NPD7320	Approved
0.8172	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5175	Approved
0.8137	Intermediate Similarity	NPD5174	Approved
0.8105	Intermediate Similarity	NPD6672	Approved
0.8105	Intermediate Similarity	NPD5737	Approved
0.8095	Intermediate Similarity	NPD6372	Approved
0.8095	Intermediate Similarity	NPD6373	Approved
0.8085	Intermediate Similarity	NPD7521	Approved
0.8085	Intermediate Similarity	NPD5330	Approved
0.8085	Intermediate Similarity	NPD7146	Approved
0.8085	Intermediate Similarity	NPD6684	Approved
0.8085	Intermediate Similarity	NPD6409	Approved
0.8085	Intermediate Similarity	NPD7334	Approved
0.8077	Intermediate Similarity	NPD5701	Approved
0.8073	Intermediate Similarity	NPD6009	Approved
0.8073	Intermediate Similarity	NPD7115	Discovery
0.8058	Intermediate Similarity	NPD5141	Approved
0.8021	Intermediate Similarity	NPD4753	Phase 2
0.802	Intermediate Similarity	NPD4700	Approved
0.8019	Intermediate Similarity	NPD4634	Approved
0.8	Intermediate Similarity	NPD7902	Approved
0.7982	Intermediate Similarity	NPD6868	Approved
0.7981	Intermediate Similarity	NPD6008	Approved
0.798	Intermediate Similarity	NPD4629	Approved
0.798	Intermediate Similarity	NPD5210	Approved
0.7944	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6903	Approved
0.7895	Intermediate Similarity	NPD5279	Phase 3
0.7895	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3668	Phase 3
0.7857	Intermediate Similarity	NPD5281	Approved
0.7857	Intermediate Similarity	NPD5284	Approved
0.7857	Intermediate Similarity	NPD6319	Approved
0.7849	Intermediate Similarity	NPD4221	Approved
0.7849	Intermediate Similarity	NPD4223	Phase 3
0.7838	Intermediate Similarity	NPD6335	Approved
0.783	Intermediate Similarity	NPD4729	Approved
0.783	Intermediate Similarity	NPD4730	Approved
0.783	Intermediate Similarity	NPD5168	Approved
0.7807	Intermediate Similarity	NPD7604	Phase 2
0.7802	Intermediate Similarity	NPD6115	Approved
0.7802	Intermediate Similarity	NPD6114	Approved
0.7802	Intermediate Similarity	NPD6697	Approved
0.7802	Intermediate Similarity	NPD6118	Approved
0.78	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD5695	Phase 3
0.7789	Intermediate Similarity	NPD5329	Approved
0.7788	Intermediate Similarity	NPD5983	Phase 2
0.7788	Intermediate Similarity	NPD4754	Approved
0.7768	Intermediate Similarity	NPD7101	Approved
0.7768	Intermediate Similarity	NPD7100	Approved
0.7748	Intermediate Similarity	NPD6317	Approved
0.7745	Intermediate Similarity	NPD5696	Approved
0.7739	Intermediate Similarity	NPD7492	Approved
0.7708	Intermediate Similarity	NPD5690	Phase 2
0.77	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7900	Approved
0.7699	Intermediate Similarity	NPD6054	Approved
0.7685	Intermediate Similarity	NPD5247	Approved
0.7685	Intermediate Similarity	NPD5250	Approved
0.7685	Intermediate Similarity	NPD5251	Approved
0.7685	Intermediate Similarity	NPD5135	Approved
0.7685	Intermediate Similarity	NPD5169	Approved
0.7685	Intermediate Similarity	NPD5248	Approved
0.7685	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5249	Phase 3
0.7684	Intermediate Similarity	NPD4197	Approved
0.7679	Intermediate Similarity	NPD6314	Approved
0.7679	Intermediate Similarity	NPD6313	Approved
0.7677	Intermediate Similarity	NPD8035	Phase 2
0.7677	Intermediate Similarity	NPD8034	Phase 2
0.7672	Intermediate Similarity	NPD6616	Approved
0.7672	Intermediate Similarity	NPD6336	Discontinued
0.7667	Intermediate Similarity	NPD6942	Approved
0.7667	Intermediate Similarity	NPD7339	Approved
0.7664	Intermediate Similarity	NPD5128	Approved
0.7658	Intermediate Similarity	NPD6274	Approved
0.7653	Intermediate Similarity	NPD6904	Approved
0.7653	Intermediate Similarity	NPD6080	Approved
0.7653	Intermediate Similarity	NPD6673	Approved
0.7642	Intermediate Similarity	NPD4768	Approved
0.7642	Intermediate Similarity	NPD4767	Approved
0.7634	Intermediate Similarity	NPD7525	Registered
0.7634	Intermediate Similarity	NPD4695	Discontinued
0.7629	Intermediate Similarity	NPD3573	Approved
0.7615	Intermediate Similarity	NPD5217	Approved
0.7615	Intermediate Similarity	NPD5215	Approved
0.7615	Intermediate Similarity	NPD5216	Approved
0.7615	Intermediate Similarity	NPD5127	Approved
0.7607	Intermediate Similarity	NPD7078	Approved
0.7582	Intermediate Similarity	NPD6117	Approved
0.7579	Intermediate Similarity	NPD4788	Approved
0.757	Intermediate Similarity	NPD6412	Phase 2
0.7565	Intermediate Similarity	NPD6370	Approved
0.7542	Intermediate Similarity	NPD7736	Approved
0.7527	Intermediate Similarity	NPD4195	Approved
0.7526	Intermediate Similarity	NPD5205	Approved
0.7526	Intermediate Similarity	NPD4689	Approved
0.7526	Intermediate Similarity	NPD4690	Approved
0.7526	Intermediate Similarity	NPD4688	Approved
0.7526	Intermediate Similarity	NPD4693	Phase 3
0.7526	Intermediate Similarity	NPD4138	Approved
0.7524	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD6116	Phase 1
0.7478	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6016	Approved
0.7478	Intermediate Similarity	NPD6015	Approved
0.7475	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3617	Approved
0.7414	Intermediate Similarity	NPD5988	Approved
0.7411	Intermediate Similarity	NPD5167	Approved
0.7391	Intermediate Similarity	NPD6059	Approved
0.7391	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5208	Approved
0.7363	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6001	Approved
0.7347	Intermediate Similarity	NPD6098	Approved
0.7347	Intermediate Similarity	NPD5280	Approved
0.7347	Intermediate Similarity	NPD4694	Approved
0.7328	Intermediate Similarity	NPD6908	Approved
0.7328	Intermediate Similarity	NPD6909	Approved
0.7327	Intermediate Similarity	NPD6050	Approved
0.7327	Intermediate Similarity	NPD5694	Approved
0.7327	Intermediate Similarity	NPD6411	Approved
0.7327	Intermediate Similarity	NPD7637	Suspended
0.7327	Intermediate Similarity	NPD5693	Phase 1
0.7311	Intermediate Similarity	NPD8293	Discontinued
0.7245	Intermediate Similarity	NPD1694	Approved
0.7245	Intermediate Similarity	NPD5363	Approved
0.7238	Intermediate Similarity	NPD4225	Approved
0.7238	Intermediate Similarity	NPD5290	Discontinued
0.7228	Intermediate Similarity	NPD5692	Phase 3
0.7228	Intermediate Similarity	NPD5785	Approved
0.7228	Intermediate Similarity	NPD5207	Approved
0.7222	Intermediate Similarity	NPD4691	Approved
0.7222	Intermediate Similarity	NPD4747	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7174	Intermediate Similarity	NPD4058	Approved
0.7172	Intermediate Similarity	NPD4623	Approved
0.7172	Intermediate Similarity	NPD4519	Discontinued
0.7143	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4809	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