NPASS Compound

Structure

NPC469810 OpenBabel07101719512D 39 44 0 0 1 0 0 0 0 0999 V2000 6.5173 4.2049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4825 2.8668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9721 5.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1300 3.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9651 0.5315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3861 0.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1579 1.7674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5193 -2.0715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0951 -2.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9374 4.0616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8063 3.0938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6915 -0.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3455 1.2069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0009 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 0.1772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3729 1.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6136 3.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8410 4.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9026 2.7235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0672 -0.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7715 1.7557 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6915 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9766 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3849 -0.6166 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7258 0.6535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6427 1.4436 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4645 -1.8258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2140 0.5980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0722 1.3794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7791 -1.1301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8458 0.4883 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 -3.9594 -0.8370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2047 -2.7672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4097 -1.5801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2771 -1.0138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3285 1.5457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 5 22 1 0 0 0 0 6 30 1 0 0 0 0 9 37 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 30 1 0 0 0 0 16 26 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 17 31 1 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 6 0 0 0 21 23 1 0 0 0 0 22 35 2 0 0 0 0 22 38 1 0 0 0 0 23 31 1 1 0 0 0 24 30 1 6 0 0 0 24 33 1 0 0 0 0 25 32 1 1 0 0 0 25 34 1 0 0 0 0 26 32 1 1 0 0 0 26 38 1 0 0 0 0 27 34 1 6 0 0 0 27 39 1 0 0 0 0 28 33 1 6 0 0 0 28 39 1 0 0 0 0 29 32 1 0 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 32 8 1 1 0 0 0 33 34 1 6 0 0 0 34 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.38
Volume:	581.323
LogP:	6.28
LogD:	5.01
LogS:	-6.397
# Rotatable Bonds:	9
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	6.215
Fsp3:	0.882
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203
MDCK Permeability:	1.640606569708325e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.135
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.283
Plasma Protein Binding (PPB):	93.97583770751953%
Volume Distribution (VD):	1.366
Pgp-substrate:	3.3197383880615234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.808

ADMET: Excretion

Clearance (CL):	5.833
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.972
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.416
Skin Sensitization:	0.907
Carcinogencity:	0.229
Eye Corrosion:	0.222
Eye Irritation:	0.066
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC469810

Natural Product ID:	NPC469810
*Common Name:**	JISKPKRVVHQSMV-ISIDXMIOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JISKPKRVVHQSMV-ISIDXMIOSA-N
Standard InCHI:	InChI=1S/C34H52O5/c1-19(2)20(3)10-11-21(4)23-14-15-30(6)24-12-13-25-32(8,29(36)37-9)26(38-22(5)35)16-27-34(25)18-33(24,34)28(39-27)17-31(23,30)7/h19,21,23-28H,3,10-18H2,1-2,4-9H3/t21-,23-,24+,25+,26+,27+,28-,30+,31-,32+,33+,34-/m1/s1
SMILES:	CC(C)C(=C)CCC(C)C1CCC2(C1(CC3C45C2CCC6C4(C5)C(O3)CC(C6(C)C(=O)OC)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL119505
PubChem CID:	10745022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	77.77	uM	PMID[570909]

☑ 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 NPC469810 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	283
0.1-0.2	2185
0.2-0.3	7204
0.3-0.4	14657
0.4-0.5	6528
0.5-0.6	5786
0.6-0.7	5037
0.7-0.8	921
0.8-0.85	83
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC124544
0.9462	High Similarity	NPC472028
0.9362	High Similarity	NPC94906
0.9062	High Similarity	NPC75941
0.8958	High Similarity	NPC41971
0.8958	High Similarity	NPC37047
0.8958	High Similarity	NPC180733
0.8936	High Similarity	NPC263135
0.8936	High Similarity	NPC288906
0.8817	High Similarity	NPC470230
0.875	High Similarity	NPC253586
0.8646	High Similarity	NPC234564
0.8602	High Similarity	NPC471043
0.8571	High Similarity	NPC108371
0.8542	High Similarity	NPC470229
0.8485	Intermediate Similarity	NPC46848
0.8485	Intermediate Similarity	NPC71706
0.8462	Intermediate Similarity	NPC270586
0.8454	Intermediate Similarity	NPC329910
0.8454	Intermediate Similarity	NPC327788
0.8438	Intermediate Similarity	NPC475118
0.8421	Intermediate Similarity	NPC471901
0.84	Intermediate Similarity	NPC214946
0.84	Intermediate Similarity	NPC304832
0.84	Intermediate Similarity	NPC275990
0.84	Intermediate Similarity	NPC76866
0.84	Intermediate Similarity	NPC271980
0.84	Intermediate Similarity	NPC246736
0.84	Intermediate Similarity	NPC88203
0.84	Intermediate Similarity	NPC193934
0.84	Intermediate Similarity	NPC148628
0.84	Intermediate Similarity	NPC286519
0.837	Intermediate Similarity	NPC98270
0.8351	Intermediate Similarity	NPC470232
0.8351	Intermediate Similarity	NPC266431
0.8333	Intermediate Similarity	NPC471902
0.8333	Intermediate Similarity	NPC287118
0.8333	Intermediate Similarity	NPC473690
0.8317	Intermediate Similarity	NPC470310
0.8317	Intermediate Similarity	NPC312900
0.83	Intermediate Similarity	NPC289148
0.83	Intermediate Similarity	NPC163963
0.83	Intermediate Similarity	NPC52899
0.8298	Intermediate Similarity	NPC146937
0.8283	Intermediate Similarity	NPC119036
0.8283	Intermediate Similarity	NPC28864
0.8283	Intermediate Similarity	NPC38296
0.8283	Intermediate Similarity	NPC38471
0.8283	Intermediate Similarity	NPC471038
0.8283	Intermediate Similarity	NPC98837
0.8283	Intermediate Similarity	NPC474793
0.8283	Intermediate Similarity	NPC20479
0.8283	Intermediate Similarity	NPC162459
0.8261	Intermediate Similarity	NPC475509
0.8247	Intermediate Similarity	NPC470385
0.8247	Intermediate Similarity	NPC47853
0.8247	Intermediate Similarity	NPC470386
0.8229	Intermediate Similarity	NPC475416
0.8229	Intermediate Similarity	NPC476934
0.82	Intermediate Similarity	NPC287676
0.82	Intermediate Similarity	NPC293866
0.8182	Intermediate Similarity	NPC111187
0.8182	Intermediate Similarity	NPC96839
0.8182	Intermediate Similarity	NPC190080
0.8173	Intermediate Similarity	NPC163216
0.8173	Intermediate Similarity	NPC211224
0.8155	Intermediate Similarity	NPC265127
0.8155	Intermediate Similarity	NPC138908
0.8155	Intermediate Similarity	NPC295366
0.8155	Intermediate Similarity	NPC37600
0.8155	Intermediate Similarity	NPC200957
0.8152	Intermediate Similarity	NPC473742
0.8137	Intermediate Similarity	NPC87927
0.8119	Intermediate Similarity	NPC121218
0.8119	Intermediate Similarity	NPC253886
0.8119	Intermediate Similarity	NPC236585
0.8119	Intermediate Similarity	NPC39683
0.8113	Intermediate Similarity	NPC470311
0.8113	Intermediate Similarity	NPC470281
0.8111	Intermediate Similarity	NPC47808
0.8105	Intermediate Similarity	NPC4309
0.81	Intermediate Similarity	NPC78427
0.81	Intermediate Similarity	NPC469986
0.81	Intermediate Similarity	NPC89099
0.81	Intermediate Similarity	NPC16911
0.8095	Intermediate Similarity	NPC257082
0.8095	Intermediate Similarity	NPC285298
0.8085	Intermediate Similarity	NPC302111
0.8085	Intermediate Similarity	NPC471042
0.8081	Intermediate Similarity	NPC29410
0.8081	Intermediate Similarity	NPC470387
0.8081	Intermediate Similarity	NPC200054
0.8077	Intermediate Similarity	NPC263729
0.8077	Intermediate Similarity	NPC176949
0.8077	Intermediate Similarity	NPC166993
0.8077	Intermediate Similarity	NPC61071
0.8077	Intermediate Similarity	NPC201908
0.8058	Intermediate Similarity	NPC244247
0.8058	Intermediate Similarity	NPC98603
0.8058	Intermediate Similarity	NPC201763
0.8058	Intermediate Similarity	NPC328737
0.8058	Intermediate Similarity	NPC84928
0.8041	Intermediate Similarity	NPC211403
0.8041	Intermediate Similarity	NPC198242
0.8039	Intermediate Similarity	NPC170615
0.8021	Intermediate Similarity	NPC57954
0.8021	Intermediate Similarity	NPC213832
0.802	Intermediate Similarity	NPC267921
0.8	Intermediate Similarity	NPC10864
0.8	Intermediate Similarity	NPC218123
0.8	Intermediate Similarity	NPC112895
0.8	Intermediate Similarity	NPC231278
0.8	Intermediate Similarity	NPC273155
0.7981	Intermediate Similarity	NPC285927
0.798	Intermediate Similarity	NPC279974
0.798	Intermediate Similarity	NPC98639
0.798	Intermediate Similarity	NPC205173
0.7979	Intermediate Similarity	NPC474971
0.7963	Intermediate Similarity	NPC52634
0.7961	Intermediate Similarity	NPC139347
0.7961	Intermediate Similarity	NPC122811
0.7961	Intermediate Similarity	NPC216114
0.7961	Intermediate Similarity	NPC469985
0.7961	Intermediate Similarity	NPC277074
0.7961	Intermediate Similarity	NPC209298
0.7959	Intermediate Similarity	NPC294263
0.7959	Intermediate Similarity	NPC244356
0.7959	Intermediate Similarity	NPC224060
0.7957	Intermediate Similarity	NPC471037
0.7944	Intermediate Similarity	NPC272242
0.7941	Intermediate Similarity	NPC471790
0.7941	Intermediate Similarity	NPC295276
0.7941	Intermediate Similarity	NPC289670
0.7938	Intermediate Similarity	NPC10274
0.7925	Intermediate Similarity	NPC471250
0.7917	Intermediate Similarity	NPC471900
0.7905	Intermediate Similarity	NPC96333
0.7905	Intermediate Similarity	NPC220974
0.7905	Intermediate Similarity	NPC88833
0.7905	Intermediate Similarity	NPC59530
0.79	Intermediate Similarity	NPC13949
0.7885	Intermediate Similarity	NPC47281
0.7885	Intermediate Similarity	NPC101842
0.7885	Intermediate Similarity	NPC471293
0.7885	Intermediate Similarity	NPC13149
0.7885	Intermediate Similarity	NPC301787
0.7879	Intermediate Similarity	NPC469982
0.7879	Intermediate Similarity	NPC224410
0.7879	Intermediate Similarity	NPC100257
0.7872	Intermediate Similarity	NPC299963
0.7872	Intermediate Similarity	NPC319909
0.787	Intermediate Similarity	NPC476964
0.7864	Intermediate Similarity	NPC473788
0.7864	Intermediate Similarity	NPC475558
0.7857	Intermediate Similarity	NPC160506
0.7857	Intermediate Similarity	NPC250753
0.785	Intermediate Similarity	NPC124053
0.785	Intermediate Similarity	NPC255655
0.785	Intermediate Similarity	NPC130302
0.7849	Intermediate Similarity	NPC13494
0.7843	Intermediate Similarity	NPC477656
0.7843	Intermediate Similarity	NPC470388
0.7835	Intermediate Similarity	NPC61688
0.7835	Intermediate Similarity	NPC24705
0.7835	Intermediate Similarity	NPC56962
0.7835	Intermediate Similarity	NPC11611
0.7835	Intermediate Similarity	NPC269267
0.783	Intermediate Similarity	NPC469845
0.7826	Intermediate Similarity	NPC304194
0.7826	Intermediate Similarity	NPC170038
0.7822	Intermediate Similarity	NPC170978
0.7822	Intermediate Similarity	NPC474921
0.7818	Intermediate Similarity	NPC469794
0.7818	Intermediate Similarity	NPC72772
0.7812	Intermediate Similarity	NPC269360
0.7812	Intermediate Similarity	NPC134197
0.7812	Intermediate Similarity	NPC33768
0.7812	Intermediate Similarity	NPC264005
0.781	Intermediate Similarity	NPC231530
0.781	Intermediate Similarity	NPC475571
0.781	Intermediate Similarity	NPC472655
0.781	Intermediate Similarity	NPC278628
0.781	Intermediate Similarity	NPC28791
0.781	Intermediate Similarity	NPC50535
0.781	Intermediate Similarity	NPC222833
0.781	Intermediate Similarity	NPC4115
0.78	Intermediate Similarity	NPC217329
0.78	Intermediate Similarity	NPC210214
0.7798	Intermediate Similarity	NPC102619
0.7798	Intermediate Similarity	NPC73986
0.7788	Intermediate Similarity	NPC140723
0.7788	Intermediate Similarity	NPC222153
0.7788	Intermediate Similarity	NPC36321
0.7788	Intermediate Similarity	NPC96217
0.7778	Intermediate Similarity	NPC477855
0.7778	Intermediate Similarity	NPC475061
0.7778	Intermediate Similarity	NPC471251
0.7778	Intermediate Similarity	NPC94650
0.7767	Intermediate Similarity	NPC252614
0.7767	Intermediate Similarity	NPC148279

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 NPC469810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	2558
0.2-0.3	4109
0.3-0.4	1486
0.4-0.5	338
0.5-0.6	222
0.6-0.7	163
0.7-0.8	16
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD8034	Phase 2
0.7857	Intermediate Similarity	NPD8035	Phase 2
0.781	Intermediate Similarity	NPD6008	Approved
0.7604	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7736	Approved
0.7238	Intermediate Similarity	NPD7638	Approved
0.7234	Intermediate Similarity	NPD6697	Approved
0.7234	Intermediate Similarity	NPD6118	Approved
0.7234	Intermediate Similarity	NPD6115	Approved
0.7234	Intermediate Similarity	NPD6114	Approved
0.7182	Intermediate Similarity	NPD7320	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7167	Intermediate Similarity	NPD8293	Discontinued
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD6054	Approved
0.7094	Intermediate Similarity	NPD6059	Approved
0.7087	Intermediate Similarity	NPD6399	Phase 3
0.7083	Intermediate Similarity	NPD6616	Approved
0.7049	Intermediate Similarity	NPD7319	Approved
0.703	Intermediate Similarity	NPD6672	Approved
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6903	Approved
0.703	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD6899	Approved
0.7027	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7078	Approved
0.7021	Intermediate Similarity	NPD6117	Approved
0.7019	Intermediate Similarity	NPD7900	Approved
0.7019	Intermediate Similarity	NPD6001	Approved
0.7019	Intermediate Similarity	NPD7748	Approved
0.7019	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.6991	Remote Similarity	NPD8130	Phase 1
0.6975	Remote Similarity	NPD6370	Approved
0.6964	Remote Similarity	NPD6373	Approved
0.6964	Remote Similarity	NPD6372	Approved
0.6961	Remote Similarity	NPD5328	Approved
0.6949	Remote Similarity	NPD6319	Approved
0.6947	Remote Similarity	NPD6116	Phase 1
0.6937	Remote Similarity	NPD5701	Approved
0.6937	Remote Similarity	NPD5697	Approved
0.693	Remote Similarity	NPD8297	Approved
0.6903	Remote Similarity	NPD7290	Approved
0.6903	Remote Similarity	NPD6883	Approved
0.6903	Remote Similarity	NPD7102	Approved
0.6891	Remote Similarity	NPD6016	Approved
0.6891	Remote Similarity	NPD6015	Approved
0.687	Remote Similarity	NPD8133	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD6650	Approved
0.6842	Remote Similarity	NPD6617	Approved
0.6842	Remote Similarity	NPD6869	Approved
0.6833	Remote Similarity	NPD5988	Approved
0.6827	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD7902	Approved
0.6814	Remote Similarity	NPD6013	Approved
0.6814	Remote Similarity	NPD6012	Approved
0.6814	Remote Similarity	NPD6014	Approved
0.6809	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7507	Approved
0.6789	Remote Similarity	NPD1700	Approved
0.6783	Remote Similarity	NPD6882	Approved
0.6777	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD5777	Approved
0.6737	Remote Similarity	NPD3703	Phase 2
0.6727	Remote Similarity	NPD7632	Discontinued
0.6726	Remote Similarity	NPD6011	Approved
0.6724	Remote Similarity	NPD4632	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7115	Discovery
0.6695	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD7515	Phase 2
0.6639	Remote Similarity	NPD8328	Phase 3
0.6637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6673	Approved
0.6635	Remote Similarity	NPD6904	Approved
0.6635	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD4786	Approved
0.6609	Remote Similarity	NPD4634	Approved
0.6607	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD3573	Approved
0.6574	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5221	Approved
0.6574	Remote Similarity	NPD4697	Phase 3
0.6574	Remote Similarity	NPD5222	Approved
0.656	Remote Similarity	NPD6033	Approved
0.6555	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD4700	Approved
0.6545	Remote Similarity	NPD5285	Approved
0.6545	Remote Similarity	NPD4696	Approved
0.6545	Remote Similarity	NPD5286	Approved
0.6535	Remote Similarity	NPD4788	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5173	Approved
0.6505	Remote Similarity	NPD3618	Phase 1
0.6481	Remote Similarity	NPD5695	Phase 3
0.6476	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6101	Approved
0.6475	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD6868	Approved
0.6471	Remote Similarity	NPD3668	Phase 3
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5696	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6449	Remote Similarity	NPD5779	Approved
0.6446	Remote Similarity	NPD7101	Approved
0.6446	Remote Similarity	NPD7100	Approved
0.6436	Remote Similarity	NPD3667	Approved
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD5225	Approved
0.6421	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5207	Approved
0.64	Remote Similarity	NPD6336	Discontinued
0.64	Remote Similarity	NPD7525	Registered
0.6392	Remote Similarity	NPD3702	Approved
0.6381	Remote Similarity	NPD5208	Approved
0.6379	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5175	Approved
0.6372	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD7327	Approved
0.6356	Remote Similarity	NPD6053	Discontinued
0.6355	Remote Similarity	NPD6050	Approved
0.6355	Remote Similarity	NPD5693	Phase 1
0.6348	Remote Similarity	NPD6412	Phase 2
0.6341	Remote Similarity	NPD6921	Approved
0.6341	Remote Similarity	NPD6908	Approved
0.6341	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6909	Approved
0.6341	Remote Similarity	NPD8296	Approved
0.6341	Remote Similarity	NPD8380	Approved
0.6341	Remote Similarity	NPD8335	Approved
0.6341	Remote Similarity	NPD8379	Approved
0.6341	Remote Similarity	NPD8378	Approved
0.6339	Remote Similarity	NPD5223	Approved
0.6321	Remote Similarity	NPD6051	Approved
0.6316	Remote Similarity	NPD5141	Approved
0.6311	Remote Similarity	NPD7516	Approved
0.6306	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD4202	Approved
0.6281	Remote Similarity	NPD6317	Approved
0.6275	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5692	Phase 3
0.6261	Remote Similarity	NPD4767	Approved
0.6261	Remote Similarity	NPD4768	Approved
0.626	Remote Similarity	NPD8294	Approved
0.626	Remote Similarity	NPD8377	Approved
0.625	Remote Similarity	NPD6081	Approved
0.623	Remote Similarity	NPD6313	Approved
0.623	Remote Similarity	NPD6314	Approved
0.6228	Remote Similarity	NPD6052	Approved
0.6228	Remote Similarity	NPD4754	Approved
0.6211	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8033	Approved
0.6204	Remote Similarity	NPD5694	Approved
0.619	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD3666	Approved
0.6154	Remote Similarity	NPD3665	Phase 1
0.6154	Remote Similarity	NPD3133	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6119	Remote Similarity	NPD6333	Approved
0.6119	Remote Similarity	NPD6334	Approved
0.6111	Remote Similarity	NPD6067	Discontinued
0.6106	Remote Similarity	NPD8418	Phase 2
0.6105	Remote Similarity	NPD5360	Phase 3
0.6105	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1694	Approved
0.6078	Remote Similarity	NPD6928	Phase 2
0.6071	Remote Similarity	NPD5959	Approved
0.6064	Remote Similarity	NPD4224	Phase 2

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