NPASS Compound

Structure

NPC473998 OpenBabel07101718222D 31 34 0 0 1 0 0 0 0 0999 V2000 -8.1309 -1.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8437 -0.7386 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 -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 -4.8363 -2.9680 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 -5.5054 -2.2248 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 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 -7.1527 -1.6896 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 -6.4836 -2.4328 0.0000 C 0 0 3 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 -6.1235 -4.1270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 -3.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 16 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 27 1 0 0 0 0 13 26 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 3 1 6 0 0 0 17 20 1 0 0 0 0 18 28 2 0 0 0 0 19 15 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 31 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.31
Volume:	468.574
LogP:	4.467
LogD:	5.109
LogS:	-4.452
# Rotatable Bonds:	6
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.307
Synthetic Accessibility Score:	4.766
Fsp3:	0.852
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	1.8524742699810304e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.71
30% Bioavailability (F30%):	0.406

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.689
Plasma Protein Binding (PPB):	90.79560089111328%
Volume Distribution (VD):	0.981
Pgp-substrate:	2.65983247756958%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.394
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	6.534
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.478
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.591
Carcinogencity:	0.372
Eye Corrosion:	0.046
Eye Irritation:	0.09
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC473998

Natural Product ID:	NPC473998
*Common Name:**	24Epsilon-Hydroperoxy-6Beta-Hydroxycholesta-4,25-Dien-3-One
IUPAC Name:	(6R,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-6-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	ZCYAJVHKULICIB-ODGNHZSJSA-N
Standard InCHI:	InChI=1S/C27H42O4/c1-16(2)25(31-30)9-6-17(3)20-7-8-21-19-15-24(29)23-14-18(28)10-12-27(23,5)22(19)11-13-26(20,21)4/h14,17,19-22,24-25,29-30H,1,6-13,15H2,2-5H3/t17-,19+,20-,21+,22+,24-,25?,26-,27-/m1/s1
SMILES:	CC(CCC(C(=C)C)OO)C1CCC2C1(CCC3C2CC(C4=CC(=O)CCC34C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457756
PubChem CID:	10574683
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
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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.79	ug ml-1	PMID[538425]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.58	ug ml-1	PMID[538425]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.47	ug ml-1	PMID[538425]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.22	ug ml-1	PMID[538425]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.22	ug ml-1	PMID[538426]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.79	ug ml-1	PMID[538426]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.58	ug ml-1	PMID[538426]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.47	ug ml-1	PMID[538426]

☑ 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 NPC473998 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	162
0.1-0.2	1052
0.2-0.3	4391
0.3-0.4	12311
0.4-0.5	10279
0.5-0.6	6246
0.6-0.7	5116
0.7-0.8	2606
0.8-0.85	359
0.85-0.9	142
0.9-0.95	26
0.95-1	7

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	NPC475806
0.9425	High Similarity	NPC48010
0.9294	High Similarity	NPC471224
0.9222	High Similarity	NPC271195
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
0.9121	High Similarity	NPC249954
0.9101	High Similarity	NPC63748
0.9101	High Similarity	NPC233116
0.9091	High Similarity	NPC1015
0.9091	High Similarity	NPC31985
0.908	High Similarity	NPC475740
0.908	High Similarity	NPC58063
0.908	High Similarity	NPC317590
0.907	High Similarity	NPC474083
0.907	High Similarity	NPC470574
0.9032	High Similarity	NPC154072
0.9011	High Similarity	NPC259286
0.9	High Similarity	NPC472930
0.9	High Similarity	NPC474736
0.9	High Similarity	NPC475255
0.9	High Similarity	NPC109305
0.8989	High Similarity	NPC320026
0.8977	High Similarity	NPC471722
0.8977	High Similarity	NPC328539
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
0.8925	High Similarity	NPC103051
0.8901	High Similarity	NPC245972
0.8901	High Similarity	NPC299100
0.8901	High Similarity	NPC196485
0.8901	High Similarity	NPC111015
0.8901	High Similarity	NPC474690
0.8889	High Similarity	NPC168027
0.8889	High Similarity	NPC185936
0.8889	High Similarity	NPC272746
0.8876	High Similarity	NPC275740
0.8876	High Similarity	NPC186688
0.8876	High Similarity	NPC477943
0.8876	High Similarity	NPC268406
0.8876	High Similarity	NPC26959
0.8876	High Similarity	NPC2983
0.8876	High Similarity	NPC86319
0.8851	High Similarity	NPC469948
0.8842	High Similarity	NPC477915
0.8817	High Similarity	NPC320306
0.8817	High Similarity	NPC253826
0.8804	High Similarity	NPC180950
0.8804	High Similarity	NPC476174
0.8804	High Similarity	NPC472932
0.8778	High Similarity	NPC191684
0.8778	High Similarity	NPC85173
0.8778	High Similarity	NPC126993
0.8764	High Similarity	NPC143767
0.8764	High Similarity	NPC131470
0.875	High Similarity	NPC222613
0.875	High Similarity	NPC472985
0.875	High Similarity	NPC249187
0.875	High Similarity	NPC475022
0.875	High Similarity	NPC118648
0.875	High Similarity	NPC472986
0.875	High Similarity	NPC51014
0.875	High Similarity	NPC247957
0.8736	High Similarity	NPC161423
0.8736	High Similarity	NPC82902
0.8736	High Similarity	NPC227064
0.8736	High Similarity	NPC237712
0.8736	High Similarity	NPC472265
0.8736	High Similarity	NPC58841
0.8736	High Similarity	NPC329043
0.8736	High Similarity	NPC321187
0.8721	High Similarity	NPC151519
0.871	High Similarity	NPC472941
0.871	High Similarity	NPC301534
0.871	High Similarity	NPC471463
0.871	High Similarity	NPC250757
0.871	High Similarity	NPC117133
0.871	High Similarity	NPC456
0.8696	High Similarity	NPC292793
0.8696	High Similarity	NPC469406
0.8681	High Similarity	NPC472978
0.8667	High Similarity	NPC474245
0.8667	High Similarity	NPC472971
0.8667	High Similarity	NPC475921
0.8667	High Similarity	NPC474704
0.8667	High Similarity	NPC472970
0.8667	High Similarity	NPC123912
0.8667	High Similarity	NPC214387
0.8667	High Similarity	NPC472240
0.8667	High Similarity	NPC262858
0.8667	High Similarity	NPC472983
0.8667	High Similarity	NPC472973
0.8667	High Similarity	NPC32830
0.8667	High Similarity	NPC119416
0.866	High Similarity	NPC72255
0.866	High Similarity	NPC204833
0.866	High Similarity	NPC209502
0.8652	High Similarity	NPC141292
0.8652	High Similarity	NPC136948
0.8652	High Similarity	NPC474684
0.8652	High Similarity	NPC90652
0.8652	High Similarity	NPC142361
0.8652	High Similarity	NPC93778
0.8646	High Similarity	NPC234892
0.8646	High Similarity	NPC473424
0.8646	High Similarity	NPC293753
0.8636	High Similarity	NPC197823
0.8636	High Similarity	NPC474218
0.8632	High Similarity	NPC327431
0.8632	High Similarity	NPC476274
0.8617	High Similarity	NPC474938
0.8617	High Similarity	NPC108078
0.8617	High Similarity	NPC474785
0.8602	High Similarity	NPC469995
0.8602	High Similarity	NPC297199
0.8602	High Similarity	NPC173875
0.8602	High Similarity	NPC174948
0.8602	High Similarity	NPC318282
0.8588	High Similarity	NPC209430
0.8588	High Similarity	NPC308038
0.8588	High Similarity	NPC30986
0.8587	High Similarity	NPC12722
0.8587	High Similarity	NPC472942
0.8571	High Similarity	NPC477149
0.8571	High Similarity	NPC319077
0.8571	High Similarity	NPC97202
0.8571	High Similarity	NPC296945
0.8571	High Similarity	NPC257353
0.8571	High Similarity	NPC49958
0.8571	High Similarity	NPC183283
0.8571	High Similarity	NPC469400
0.8571	High Similarity	NPC477147
0.8571	High Similarity	NPC202167
0.8571	High Similarity	NPC214264
0.8571	High Similarity	NPC150531
0.8571	High Similarity	NPC302607
0.8571	High Similarity	NPC149047
0.8571	High Similarity	NPC171137
0.8571	High Similarity	NPC152695
0.8571	High Similarity	NPC50692
0.8571	High Similarity	NPC260268
0.8571	High Similarity	NPC476027
0.8571	High Similarity	NPC48733
0.8571	High Similarity	NPC85829
0.8571	High Similarity	NPC69622
0.8557	High Similarity	NPC311612
0.8556	High Similarity	NPC470417
0.8556	High Similarity	NPC292491
0.8556	High Similarity	NPC310752
0.8556	High Similarity	NPC193360
0.8556	High Similarity	NPC471724
0.8556	High Similarity	NPC328313
0.8542	High Similarity	NPC476223
0.8542	High Similarity	NPC476240
0.8542	High Similarity	NPC224720
0.8539	High Similarity	NPC327115
0.8539	High Similarity	NPC155011
0.8539	High Similarity	NPC94755
0.8526	High Similarity	NPC235464
0.8526	High Similarity	NPC197386
0.8526	High Similarity	NPC166745
0.8523	High Similarity	NPC476412
0.8523	High Similarity	NPC33913
0.8523	High Similarity	NPC165064
0.8511	High Similarity	NPC192428
0.8511	High Similarity	NPC7124
0.8511	High Similarity	NPC29152
0.8511	High Similarity	NPC328371
0.8506	High Similarity	NPC93590
0.8495	Intermediate Similarity	NPC472976
0.8495	Intermediate Similarity	NPC166906
0.8495	Intermediate Similarity	NPC472977
0.8488	Intermediate Similarity	NPC2482
0.8488	Intermediate Similarity	NPC472478
0.8485	Intermediate Similarity	NPC477916
0.8485	Intermediate Similarity	NPC475060
0.8485	Intermediate Similarity	NPC83744
0.8485	Intermediate Similarity	NPC220229
0.8478	Intermediate Similarity	NPC212301
0.8478	Intermediate Similarity	NPC189520
0.8478	Intermediate Similarity	NPC86266
0.8478	Intermediate Similarity	NPC155304
0.8478	Intermediate Similarity	NPC110657
0.8462	Intermediate Similarity	NPC310010
0.8462	Intermediate Similarity	NPC326627
0.8462	Intermediate Similarity	NPC469319
0.8462	Intermediate Similarity	NPC229871
0.8462	Intermediate Similarity	NPC76879

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 NPC473998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1345
0.2-0.3	3875
0.3-0.4	2621
0.4-0.5	668
0.5-0.6	160
0.6-0.7	132
0.7-0.8	151
0.8-0.85	38
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD5328	Approved
0.8966	High Similarity	NPD3618	Phase 1
0.8953	High Similarity	NPD4786	Approved
0.8889	High Similarity	NPD6079	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
0.8587	High Similarity	NPD4202	Approved
0.8511	High Similarity	NPD5220	Clinical (unspecified phase)
0.8511	High Similarity	NPD5222	Approved
0.8511	High Similarity	NPD5221	Approved
0.8511	High Similarity	NPD4697	Phase 3
0.8462	Intermediate Similarity	NPD4753	Phase 2
0.8454	Intermediate Similarity	NPD5211	Phase 2
0.8421	Intermediate Similarity	NPD5173	Approved
0.8421	Intermediate Similarity	NPD4755	Approved
0.8333	Intermediate Similarity	NPD5279	Phase 3
0.8295	Intermediate Similarity	NPD4223	Phase 3
0.8295	Intermediate Similarity	NPD4221	Approved
0.8283	Intermediate Similarity	NPD5141	Approved
0.828	Intermediate Similarity	NPD7515	Phase 2
0.8247	Intermediate Similarity	NPD5286	Approved
0.8247	Intermediate Similarity	NPD5285	Approved
0.8247	Intermediate Similarity	NPD4700	Approved
0.8247	Intermediate Similarity	NPD4696	Approved
0.8222	Intermediate Similarity	NPD5329	Approved
0.8191	Intermediate Similarity	NPD6399	Phase 3
0.8163	Intermediate Similarity	NPD5223	Approved
0.8111	Intermediate Similarity	NPD4197	Approved
0.8111	Intermediate Similarity	NPD3668	Phase 3
0.8081	Intermediate Similarity	NPD4633	Approved
0.8081	Intermediate Similarity	NPD5224	Approved
0.8081	Intermediate Similarity	NPD5225	Approved
0.8081	Intermediate Similarity	NPD5226	Approved
0.8061	Intermediate Similarity	NPD7640	Approved
0.8061	Intermediate Similarity	NPD7639	Approved
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8021	Intermediate Similarity	NPD4629	Approved
0.8021	Intermediate Similarity	NPD5210	Approved
0.802	Intermediate Similarity	NPD5739	Approved
0.802	Intermediate Similarity	NPD6402	Approved
0.802	Intermediate Similarity	NPD7128	Approved
0.802	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD4754	Approved
0.8	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD5175	Approved
0.7959	Intermediate Similarity	NPD7638	Approved
0.7957	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD5737	Approved
0.7935	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD4138	Approved
0.7935	Intermediate Similarity	NPD4689	Approved
0.7935	Intermediate Similarity	NPD4693	Phase 3
0.7935	Intermediate Similarity	NPD4623	Approved
0.7935	Intermediate Similarity	NPD4519	Discontinued
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7935	Intermediate Similarity	NPD4690	Approved
0.7935	Intermediate Similarity	NPD5205	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD4688	Approved
0.7917	Intermediate Similarity	NPD7748	Approved
0.7907	Intermediate Similarity	NPD7339	Approved
0.7907	Intermediate Similarity	NPD6942	Approved
0.7865	Intermediate Similarity	NPD7525	Registered
0.7864	Intermediate Similarity	NPD6899	Approved
0.7864	Intermediate Similarity	NPD6881	Approved
0.7864	Intermediate Similarity	NPD7320	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)
0.7802	Intermediate Similarity	NPD4788	Approved
0.7788	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD7115	Discovery
0.7767	Intermediate Similarity	NPD5701	Approved
0.7767	Intermediate Similarity	NPD5697	Approved
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD5690	Phase 2
0.7742	Intermediate Similarity	NPD4694	Approved
0.7742	Intermediate Similarity	NPD5280	Approved
0.7714	Intermediate Similarity	NPD6883	Approved
0.7714	Intermediate Similarity	NPD7102	Approved
0.7714	Intermediate Similarity	NPD7290	Approved
0.7692	Intermediate Similarity	NPD5168	Approved
0.7692	Intermediate Similarity	NPD4729	Approved
0.7692	Intermediate Similarity	NPD5128	Approved
0.7692	Intermediate Similarity	NPD6011	Approved
0.7692	Intermediate Similarity	NPD4730	Approved
0.7677	Intermediate Similarity	NPD7902	Approved
0.7667	Intermediate Similarity	NPD4695	Discontinued
0.7653	Intermediate Similarity	NPD5695	Phase 3
0.7647	Intermediate Similarity	NPD4747	Approved
0.7642	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7642	Intermediate Similarity	NPD6650	Approved
0.7642	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD6847	Approved
0.7642	Intermediate Similarity	NPD6649	Approved
0.7642	Intermediate Similarity	NPD6617	Approved
0.764	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6014	Approved
0.7619	Intermediate Similarity	NPD6012	Approved
0.7619	Intermediate Similarity	NPD6013	Approved
0.7614	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5696	Approved
0.757	Intermediate Similarity	NPD8297	Approved
0.757	Intermediate Similarity	NPD6882	Approved
0.7558	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4195	Approved
0.7547	Intermediate Similarity	NPD5169	Approved
0.7547	Intermediate Similarity	NPD5250	Approved
0.7547	Intermediate Similarity	NPD5248	Approved
0.7547	Intermediate Similarity	NPD5251	Approved
0.7547	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5247	Approved
0.7547	Intermediate Similarity	NPD4634	Approved
0.7547	Intermediate Similarity	NPD5135	Approved
0.7547	Intermediate Similarity	NPD5249	Phase 3
0.7529	Intermediate Similarity	NPD4137	Phase 3
0.7526	Intermediate Similarity	NPD5281	Approved
0.7526	Intermediate Similarity	NPD5284	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.7477	Intermediate Similarity	NPD5217	Approved
0.7477	Intermediate Similarity	NPD5216	Approved
0.7477	Intermediate Similarity	NPD5215	Approved
0.7477	Intermediate Similarity	NPD5127	Approved
0.7475	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4691	Approved
0.7429	Intermediate Similarity	NPD6412	Phase 2
0.7386	Intermediate Similarity	NPD5733	Approved
0.7379	Intermediate Similarity	NPD7632	Discontinued
0.7374	Intermediate Similarity	NPD7900	Approved
0.7374	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6868	Approved
0.7347	Intermediate Similarity	NPD5693	Phase 1
0.7347	Intermediate Similarity	NPD8035	Phase 2
0.7347	Intermediate Similarity	NPD8034	Phase 2
0.7339	Intermediate Similarity	NPD4632	Approved
0.7326	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5167	Approved
0.7245	Intermediate Similarity	NPD4096	Approved
0.7232	Intermediate Similarity	NPD6335	Approved
0.7222	Intermediate Similarity	NPD6117	Approved
0.7216	Intermediate Similarity	NPD5208	Approved
0.7207	Intermediate Similarity	NPD6274	Approved
0.7204	Intermediate Similarity	NPD4139	Approved
0.7204	Intermediate Similarity	NPD4692	Approved
0.7191	Intermediate Similarity	NPD4058	Approved
0.7191	Intermediate Similarity	NPD6924	Approved
0.7191	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4687	Approved
0.7191	Intermediate Similarity	NPD6926	Approved
0.7188	Intermediate Similarity	NPD6098	Approved
0.7184	Intermediate Similarity	NPD6404	Discontinued
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7174	Intermediate Similarity	NPD6929	Approved
0.7172	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD6008	Approved
0.7168	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD7101	Approved
0.7159	Intermediate Similarity	NPD5276	Approved
0.7159	Intermediate Similarity	NPD4243	Approved
0.7143	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD6059	Approved
0.71	Intermediate Similarity	NPD5133	Approved
0.7097	Intermediate Similarity	NPD6930	Phase 2
0.7097	Intermediate Similarity	NPD6931	Approved
0.7097	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4225	Approved
0.7087	Intermediate Similarity	NPD5290	Discontinued
0.7083	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD1696	Phase 3
0.708	Intermediate Similarity	NPD6314	Approved
0.708	Intermediate Similarity	NPD6313	Approved
0.7071	Intermediate Similarity	NPD5692	Phase 3
0.7071	Intermediate Similarity	NPD5785	Approved
0.7065	Intermediate Similarity	NPD6118	Approved
0.7065	Intermediate Similarity	NPD6697	Approved
0.7065	Intermediate Similarity	NPD6114	Approved
0.7065	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6695	Phase 3

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