NPASS Compound

Structure

NPC475806 OpenBabel07101718182D 30 33 0 0 1 0 0 0 0 0999 V2000 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3875 -4.1396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3557 -4.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2109 -3.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5417 -4.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5636 -3.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2546 -2.8795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 24 1 0 0 0 0 17 1 1 1 0 0 0 17 20 1 0 0 0 0 18 28 2 0 0 0 0 19 16 1 6 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 26 1 1 0 0 0 21 26 1 1 0 0 0 22 27 1 1 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 29 1 1 0 0 0 25 30 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.31
Volume:	459.784
LogP:	4.457
LogD:	4.954
LogS:	-4.611
# Rotatable Bonds:	4
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.661
Fsp3:	0.852
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:	-4.721
MDCK Permeability:	1.6775138647062704e-05
Pgp-inhibitor:	0.941
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.675

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.869
Plasma Protein Binding (PPB):	91.58821105957031%
Volume Distribution (VD):	1.071
Pgp-substrate:	2.459599494934082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.37
CYP2C19-inhibitor:	0.157
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.408
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.786
CYP3A4-inhibitor:	0.651
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	6.194
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.28
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.691
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.658
Skin Sensitization:	0.897
Carcinogencity:	0.152
Eye Corrosion:	0.048
Eye Irritation:	0.274
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC475806

Natural Product ID:	NPC475806
*Common Name:**	6Beta,24-Dihydroxycholesta-4,23(E)-Dien-3-One
IUPAC Name:	(6R,8S,9S,10R,13R,14S,17R)-6-hydroxy-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	KSNLRAICCKNAFF-RCMZTQOBSA-N
Standard InCHI:	InChI=1S/C27H42O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-19-16-24(29)23-15-18(28)10-13-27(23,5)22(19)11-14-26(20,21)4/h6,12,15,17,19-22,24,29-30H,7-11,13-14,16H2,1-5H3/b12-6+/t17-,19+,20-,21+,22+,24-,26-,27-/m1/s1
SMILES:	CC(CC=CC(C)(C)O)C1CCC2C1(CCC3C2CC(C4=CC(=O)CCC34C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516520
PubChem CID:	21672108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984148]
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322362]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.14	ug ml-1	PMID[479817]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.45	ug ml-1	PMID[479817]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.54	ug ml-1	PMID[479817]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.55	ug ml-1	PMID[479817]

☑ 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 NPC475806 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	161
0.1-0.2	1024
0.2-0.3	4255
0.3-0.4	12240
0.4-0.5	10317
0.5-0.6	6482
0.6-0.7	5117
0.7-0.8	2560
0.8-0.85	357
0.85-0.9	148
0.9-0.95	28
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC8993
0.9765	High Similarity	NPC473999
0.9765	High Similarity	NPC309603
0.954	High Similarity	NPC473998
0.9438	High Similarity	NPC259286
0.9438	High Similarity	NPC271195
0.9425	High Similarity	NPC48010
0.9333	High Similarity	NPC249954
0.931	High Similarity	NPC2983
0.9302	High Similarity	NPC58063
0.9294	High Similarity	NPC471224
0.9213	High Similarity	NPC474736
0.9213	High Similarity	NPC69454
0.9186	High Similarity	NPC474733
0.9186	High Similarity	NPC474778
0.9186	High Similarity	NPC31564
0.9186	High Similarity	NPC474732
0.9186	High Similarity	NPC145879
0.9176	High Similarity	NPC214043
0.9176	High Similarity	NPC85774
0.913	High Similarity	NPC103051
0.9111	High Similarity	NPC299100
0.9101	High Similarity	NPC63748
0.9101	High Similarity	NPC272746
0.9101	High Similarity	NPC233116
0.908	High Similarity	NPC475740
0.907	High Similarity	NPC474083
0.907	High Similarity	NPC470574
0.9032	High Similarity	NPC154072
0.9011	High Similarity	NPC180950
0.9	High Similarity	NPC109305
0.8989	High Similarity	NPC320026
0.8977	High Similarity	NPC471722
0.8977	High Similarity	NPC328539
0.8966	High Similarity	NPC475022
0.8966	High Similarity	NPC118648
0.8966	High Similarity	NPC222613
0.8966	High Similarity	NPC72133
0.8966	High Similarity	NPC469994
0.8953	High Similarity	NPC473246
0.8953	High Similarity	NPC221758
0.8953	High Similarity	NPC59453
0.8947	High Similarity	NPC249187
0.8947	High Similarity	NPC247957
0.8901	High Similarity	NPC292793
0.8901	High Similarity	NPC474690
0.8876	High Similarity	NPC275740
0.8876	High Similarity	NPC1015
0.8876	High Similarity	NPC472973
0.8876	High Similarity	NPC186688
0.8876	High Similarity	NPC268406
0.8876	High Similarity	NPC31985
0.8876	High Similarity	NPC26959
0.8876	High Similarity	NPC86319
0.8864	High Similarity	NPC93778
0.8864	High Similarity	NPC141292
0.8851	High Similarity	NPC469948
0.8842	High Similarity	NPC477915
0.8817	High Similarity	NPC474785
0.8817	High Similarity	NPC474938
0.8791	High Similarity	NPC475255
0.8791	High Similarity	NPC472930
0.8778	High Similarity	NPC191684
0.8778	High Similarity	NPC85173
0.8778	High Similarity	NPC126993
0.8764	High Similarity	NPC143767
0.8764	High Similarity	NPC292491
0.8764	High Similarity	NPC131470
0.8764	High Similarity	NPC310752
0.8764	High Similarity	NPC193360
0.8763	High Similarity	NPC257353
0.875	High Similarity	NPC472985
0.875	High Similarity	NPC51014
0.875	High Similarity	NPC472986
0.875	High Similarity	NPC311612
0.8736	High Similarity	NPC476412
0.8736	High Similarity	NPC161423
0.8736	High Similarity	NPC82902
0.8736	High Similarity	NPC227064
0.8736	High Similarity	NPC329043
0.8736	High Similarity	NPC472265
0.8736	High Similarity	NPC58841
0.8736	High Similarity	NPC237712
0.8736	High Similarity	NPC33913
0.8736	High Similarity	NPC321187
0.8721	High Similarity	NPC151519
0.871	High Similarity	NPC301534
0.871	High Similarity	NPC471463
0.871	High Similarity	NPC250757
0.8696	High Similarity	NPC111015
0.8696	High Similarity	NPC196485
0.8696	High Similarity	NPC245972
0.8681	High Similarity	NPC185936
0.8681	High Similarity	NPC472978
0.8681	High Similarity	NPC168027
0.8667	High Similarity	NPC477943
0.8667	High Similarity	NPC474245
0.8667	High Similarity	NPC262858
0.8667	High Similarity	NPC472971
0.8667	High Similarity	NPC262043
0.8667	High Similarity	NPC472970
0.8667	High Similarity	NPC472240
0.8667	High Similarity	NPC32830
0.8667	High Similarity	NPC119416
0.8667	High Similarity	NPC76879
0.866	High Similarity	NPC72255
0.866	High Similarity	NPC204833
0.866	High Similarity	NPC209502
0.8652	High Similarity	NPC136948
0.8652	High Similarity	NPC474684
0.8652	High Similarity	NPC90652
0.8652	High Similarity	NPC317590
0.8652	High Similarity	NPC287079
0.8652	High Similarity	NPC136548
0.8652	High Similarity	NPC142361
0.8646	High Similarity	NPC87351
0.8646	High Similarity	NPC473424
0.8636	High Similarity	NPC474218
0.8636	High Similarity	NPC476426
0.8617	High Similarity	NPC253826
0.8617	High Similarity	NPC126815
0.8617	High Similarity	NPC108078
0.8617	High Similarity	NPC320306
0.8617	High Similarity	NPC107243
0.8605	High Similarity	NPC264245
0.8602	High Similarity	NPC476174
0.8602	High Similarity	NPC472932
0.8588	High Similarity	NPC209430
0.8588	High Similarity	NPC308038
0.8588	High Similarity	NPC30986
0.8587	High Similarity	NPC12722
0.8587	High Similarity	NPC474807
0.8571	High Similarity	NPC319077
0.8571	High Similarity	NPC97202
0.8571	High Similarity	NPC49958
0.8571	High Similarity	NPC302607
0.8571	High Similarity	NPC183283
0.8571	High Similarity	NPC202167
0.8571	High Similarity	NPC214264
0.8571	High Similarity	NPC150531
0.8571	High Similarity	NPC149047
0.8571	High Similarity	NPC469400
0.8571	High Similarity	NPC171137
0.8571	High Similarity	NPC152695
0.8571	High Similarity	NPC48733
0.8571	High Similarity	NPC50692
0.8571	High Similarity	NPC260268
0.8571	High Similarity	NPC476027
0.8571	High Similarity	NPC85829
0.8571	High Similarity	NPC296945
0.8571	High Similarity	NPC69622
0.8556	High Similarity	NPC470417
0.8556	High Similarity	NPC471724
0.8556	High Similarity	NPC328313
0.8542	High Similarity	NPC282524
0.8542	High Similarity	NPC476223
0.8542	High Similarity	NPC476240
0.8542	High Similarity	NPC224720
0.8539	High Similarity	NPC194417
0.8539	High Similarity	NPC473168
0.8539	High Similarity	NPC327115
0.8539	High Similarity	NPC155011
0.8539	High Similarity	NPC472974
0.8539	High Similarity	NPC94755
0.8523	High Similarity	NPC165064
0.8511	High Similarity	NPC160056
0.8511	High Similarity	NPC472941
0.8511	High Similarity	NPC117133
0.8511	High Similarity	NPC456
0.8506	High Similarity	NPC93590
0.8506	High Similarity	NPC296701
0.8506	High Similarity	NPC49964
0.8506	High Similarity	NPC218616
0.8506	High Similarity	NPC193347
0.8506	High Similarity	NPC145143
0.8506	High Similarity	NPC87489
0.85	High Similarity	NPC214644
0.8495	Intermediate Similarity	NPC472976
0.8495	Intermediate Similarity	NPC469406
0.8495	Intermediate Similarity	NPC472977
0.8488	Intermediate Similarity	NPC164840
0.8488	Intermediate Similarity	NPC241290
0.8488	Intermediate Similarity	NPC2482
0.8488	Intermediate Similarity	NPC476809
0.8488	Intermediate Similarity	NPC209944
0.8488	Intermediate Similarity	NPC234193
0.8488	Intermediate Similarity	NPC472478
0.8485	Intermediate Similarity	NPC475060
0.8485	Intermediate Similarity	NPC83744
0.8485	Intermediate Similarity	NPC220229
0.8485	Intermediate Similarity	NPC185
0.8485	Intermediate Similarity	NPC477916
0.8478	Intermediate Similarity	NPC472975
0.8471	Intermediate Similarity	NPC275494
0.8471	Intermediate Similarity	NPC82635
0.8471	Intermediate Similarity	NPC471409
0.8462	Intermediate Similarity	NPC472475
0.8462	Intermediate Similarity	NPC474704
0.8462	Intermediate Similarity	NPC310010
0.8462	Intermediate Similarity	NPC326627

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 NPC475806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1296
0.2-0.3	3798
0.3-0.4	2669
0.4-0.5	728
0.5-0.6	168
0.6-0.7	122
0.7-0.8	163
0.8-0.85	40
0.85-0.9	18
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9101	High Similarity	NPD6079	Approved
0.9091	High Similarity	NPD5328	Approved
0.8966	High Similarity	NPD3618	Phase 1
0.8953	High Similarity	NPD4786	Approved
0.8791	High Similarity	NPD4202	Approved
0.8736	High Similarity	NPD3666	Approved
0.8736	High Similarity	NPD3665	Phase 1
0.8736	High Similarity	NPD3133	Approved
0.8721	High Similarity	NPD3667	Approved
0.8646	High Similarity	NPD5211	Phase 2
0.8511	High Similarity	NPD5220	Clinical (unspecified phase)
0.8511	High Similarity	NPD5222	Approved
0.8511	High Similarity	NPD5221	Approved
0.8506	High Similarity	NPD4221	Approved
0.8506	High Similarity	NPD4223	Phase 3
0.8469	Intermediate Similarity	NPD5141	Approved
0.8462	Intermediate Similarity	NPD4753	Phase 2
0.8438	Intermediate Similarity	NPD4696	Approved
0.8438	Intermediate Similarity	NPD5286	Approved
0.8438	Intermediate Similarity	NPD5285	Approved
0.8427	Intermediate Similarity	NPD5329	Approved
0.8421	Intermediate Similarity	NPD5173	Approved
0.8421	Intermediate Similarity	NPD4755	Approved
0.8351	Intermediate Similarity	NPD5223	Approved
0.8333	Intermediate Similarity	NPD5279	Phase 3
0.8333	Intermediate Similarity	NPD4519	Discontinued
0.8333	Intermediate Similarity	NPD4623	Approved
0.8316	Intermediate Similarity	NPD4697	Phase 3
0.8315	Intermediate Similarity	NPD4197	Approved
0.8265	Intermediate Similarity	NPD5225	Approved
0.8265	Intermediate Similarity	NPD5224	Approved
0.8265	Intermediate Similarity	NPD4633	Approved
0.8265	Intermediate Similarity	NPD5226	Approved
0.8247	Intermediate Similarity	NPD4700	Approved
0.8211	Intermediate Similarity	NPD5210	Approved
0.8211	Intermediate Similarity	NPD4629	Approved
0.8182	Intermediate Similarity	NPD5175	Approved
0.8182	Intermediate Similarity	NPD5174	Approved
0.8132	Intermediate Similarity	NPD4138	Approved
0.8132	Intermediate Similarity	NPD4693	Phase 3
0.8132	Intermediate Similarity	NPD4688	Approved
0.8132	Intermediate Similarity	NPD4690	Approved
0.8132	Intermediate Similarity	NPD4689	Approved
0.8132	Intermediate Similarity	NPD5690	Phase 2
0.8132	Intermediate Similarity	NPD5205	Approved
0.8085	Intermediate Similarity	NPD7515	Phase 2
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD6899	Approved
0.8039	Intermediate Similarity	NPD6881	Approved
0.802	Intermediate Similarity	NPD6675	Approved
0.802	Intermediate Similarity	NPD5739	Approved
0.802	Intermediate Similarity	NPD6402	Approved
0.802	Intermediate Similarity	NPD7128	Approved
0.8	Intermediate Similarity	NPD4754	Approved
0.8	Intermediate Similarity	NPD4788	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7955	Intermediate Similarity	NPD4195	Approved
0.7944	Intermediate Similarity	NPD7115	Discovery
0.7941	Intermediate Similarity	NPD5697	Approved
0.7935	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD4694	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD5280	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7912	Intermediate Similarity	NPD3668	Phase 3
0.7907	Intermediate Similarity	NPD7339	Approved
0.7907	Intermediate Similarity	NPD6942	Approved
0.7885	Intermediate Similarity	NPD7102	Approved
0.7885	Intermediate Similarity	NPD7290	Approved
0.7885	Intermediate Similarity	NPD6883	Approved
0.7879	Intermediate Similarity	NPD7640	Approved
0.7879	Intermediate Similarity	NPD7639	Approved
0.7865	Intermediate Similarity	NPD7525	Registered
0.7864	Intermediate Similarity	NPD4729	Approved
0.7864	Intermediate Similarity	NPD4730	Approved
0.7864	Intermediate Similarity	NPD7320	Approved
0.7864	Intermediate Similarity	NPD6011	Approved
0.7843	Intermediate Similarity	NPD4767	Approved
0.7843	Intermediate Similarity	NPD4768	Approved
0.7841	Intermediate Similarity	NPD3617	Approved
0.7826	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6650	Approved
0.781	Intermediate Similarity	NPD6649	Approved
0.781	Intermediate Similarity	NPD6617	Approved
0.781	Intermediate Similarity	NPD6869	Approved
0.781	Intermediate Similarity	NPD8130	Phase 1
0.781	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6373	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD7638	Approved
0.7767	Intermediate Similarity	NPD5701	Approved
0.7766	Intermediate Similarity	NPD5737	Approved
0.7766	Intermediate Similarity	NPD6672	Approved
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7736	Intermediate Similarity	NPD6882	Approved
0.7736	Intermediate Similarity	NPD8297	Approved
0.7732	Intermediate Similarity	NPD7748	Approved
0.7714	Intermediate Similarity	NPD5169	Approved
0.7714	Intermediate Similarity	NPD5248	Approved
0.7714	Intermediate Similarity	NPD5247	Approved
0.7714	Intermediate Similarity	NPD4634	Approved
0.7714	Intermediate Similarity	NPD5135	Approved
0.7714	Intermediate Similarity	NPD5251	Approved
0.7714	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5250	Approved
0.7714	Intermediate Similarity	NPD5249	Phase 3
0.7708	Intermediate Similarity	NPD5284	Approved
0.7708	Intermediate Similarity	NPD5281	Approved
0.7692	Intermediate Similarity	NPD5168	Approved
0.7692	Intermediate Similarity	NPD5128	Approved
0.766	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5695	Phase 3
0.7647	Intermediate Similarity	NPD4747	Approved
0.7642	Intermediate Similarity	NPD5127	Approved
0.7642	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5216	Approved
0.7642	Intermediate Similarity	NPD5215	Approved
0.7642	Intermediate Similarity	NPD5217	Approved
0.764	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5696	Approved
0.7558	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4137	Phase 3
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.7475	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4695	Discontinued
0.7442	Intermediate Similarity	NPD4691	Approved
0.7431	Intermediate Similarity	NPD5167	Approved
0.7423	Intermediate Similarity	NPD4096	Approved
0.7396	Intermediate Similarity	NPD4518	Approved
0.7396	Intermediate Similarity	NPD5208	Approved
0.7391	Intermediate Similarity	NPD4692	Approved
0.7391	Intermediate Similarity	NPD4139	Approved
0.7387	Intermediate Similarity	NPD6335	Approved
0.7386	Intermediate Similarity	NPD6924	Approved
0.7386	Intermediate Similarity	NPD4785	Approved
0.7386	Intermediate Similarity	NPD5733	Approved
0.7386	Intermediate Similarity	NPD4058	Approved
0.7386	Intermediate Similarity	NPD4687	Approved
0.7386	Intermediate Similarity	NPD4784	Approved
0.7386	Intermediate Similarity	NPD6926	Approved
0.7368	Intermediate Similarity	NPD6098	Approved
0.7364	Intermediate Similarity	NPD6868	Approved
0.7356	Intermediate Similarity	NPD4243	Approved
0.7347	Intermediate Similarity	NPD5693	Phase 1
0.7326	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7100	Approved
0.7321	Intermediate Similarity	NPD7101	Approved
0.7297	Intermediate Similarity	NPD6317	Approved
0.7297	Intermediate Similarity	NPD6009	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.7283	Intermediate Similarity	NPD6930	Phase 2
0.7283	Intermediate Similarity	NPD7514	Phase 3
0.7283	Intermediate Similarity	NPD6931	Approved
0.7273	Intermediate Similarity	NPD5133	Approved
0.7264	Intermediate Similarity	NPD6412	Phase 2
0.7263	Intermediate Similarity	NPD1696	Phase 3
0.7257	Intermediate Similarity	NPD6054	Approved
0.7255	Intermediate Similarity	NPD5290	Discontinued
0.7253	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5207	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7232	Intermediate Similarity	NPD6314	Approved
0.7222	Intermediate Similarity	NPD6933	Approved
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.7212	Intermediate Similarity	NPD5091	Approved
0.7209	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5360	Phase 3
0.7207	Intermediate Similarity	NPD6274	Approved
0.72	Intermediate Similarity	NPD6001	Approved
0.72	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7900	Approved
0.7191	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6404	Discontinued
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7174	Intermediate Similarity	NPD6929	Approved
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD5694	Approved
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.7172	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD6008	Approved
0.7159	Intermediate Similarity	NPD7150	Approved
0.7159	Intermediate Similarity	NPD5276	Approved
0.7159	Intermediate Similarity	NPD7152	Approved
0.7159	Intermediate Similarity	NPD7151	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