NPASS Compound

Structure

NPC475305 OpenBabel07101718322D 41 44 0 0 1 0 0 0 0 0999 V2000 -5.0291 -7.0234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3876 -3.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2136 -6.2966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4673 -4.2360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 -3.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1943 -0.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7961 1.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7052 -3.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7686 -0.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7686 -1.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8899 -6.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7472 -3.1269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9502 -1.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9276 0.2584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9822 -5.6922 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.7871 -3.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6892 -2.2861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2562 -0.6625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6570 1.0100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6773 -2.7498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0750 -0.2188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0750 -1.1965 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5464 0.6038 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6570 -2.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5464 -2.0191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6892 0.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4819 -1.2596 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8430 -4.7243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1468 -2.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9218 -0.7077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9502 0.2305 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6747 -0.7077 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1831 -2.2853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 1.3428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 1.7602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6116 -4.1199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4666 -1.6490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5098 -2.2369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9353 -4.3609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 -2.7581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 8 20 1 0 0 0 0 9 30 1 0 0 0 0 10 30 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 14 31 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 24 1 0 0 0 0 18 6 1 1 0 0 0 18 27 1 0 0 0 0 19 7 1 1 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 33 2 0 0 0 0 20 38 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 6 0 0 0 22 25 1 0 0 0 0 22 30 1 6 0 0 0 23 34 1 1 0 0 0 24 25 1 0 0 0 0 24 39 1 1 0 0 0 25 40 1 1 0 0 0 26 31 1 0 0 0 0 26 35 2 0 0 0 0 27 32 1 1 0 0 0 27 38 1 0 0 0 0 28 36 2 0 0 0 0 28 39 1 0 0 0 0 29 37 2 0 0 0 0 29 40 1 0 0 0 0 31 32 1 6 0 0 0 31 41 1 0 0 0 0 32 13 1 6 0 0 0 32 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.31
Volume:	591.095
LogP:	4.548
LogD:	4.183
LogS:	-4.776
# Rotatable Bonds:	9
TPSA:	128.73
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.164
Synthetic Accessibility Score:	6.019
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.083
MDCK Permeability:	6.251568993320689e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.468
Human Intestinal Absorption (HIA):	0.195
20% Bioavailability (F20%):	0.497
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	85.78466033935547%
Volume Distribution (VD):	2.457
Pgp-substrate:	7.188786506652832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.124
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	8.653
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.891
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.707
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.235
Carcinogencity:	0.074
Eye Corrosion:	0.029
Eye Irritation:	0.021
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC475305

Natural Product ID:	NPC475305
*Common Name:**	BSRAURHKNCOHAJ-DHZVKXSHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BSRAURHKNCOHAJ-DHZVKXSHSA-N
Standard InCHI:	InChI=1S/C32H46O9/c1-11-15(3)28(36)39-24-17(5)13-32-27(38-20(8)33)18(6)14-31(32,41-32)26(35)19(7)23(34)21-22(30(21,9)10)25(24)40-29(37)16(4)12-2/h12-13,15,18-19,21-25,27,34H,11,14H2,1-10H3/b16-12+,17-13+/t15?,18-,19+,21-,22+,23-,24+,25-,27-,31-,32-/m0/s1
SMILES:	CCC(C(=O)O[C@@H]1/C(=C/[C@]23O[C@@]3(C[C@@H]([C@@H]2OC(=O)C)C)C(=O)[C@@H]([C@@H]([C@@H]2[C@H]([C@@H]1OC(=O)/C(=C/C)/C)C2(C)C)O)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503230
PubChem CID:	44559779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	>	1000.0	ug	PMID[535810]

☑ 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 NPC475305 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	285
0.1-0.2	1748
0.2-0.3	5860
0.3-0.4	9943
0.4-0.5	13045
0.5-0.6	7029
0.6-0.7	3740
0.7-0.8	939
0.8-0.85	72
0.85-0.9	8
0.9-0.95	9
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC475401
0.9817	High Similarity	NPC477092
0.9626	High Similarity	NPC473522
0.9626	High Similarity	NPC475277
0.9626	High Similarity	NPC477093
0.9533	High Similarity	NPC475495
0.8692	High Similarity	NPC471767
0.8692	High Similarity	NPC477356
0.8636	High Similarity	NPC470192
0.8611	High Similarity	NPC250594
0.8611	High Similarity	NPC471757
0.8611	High Similarity	NPC118405
0.8611	High Similarity	NPC49393
0.8611	High Similarity	NPC105725
0.8611	High Similarity	NPC78127
0.8505	High Similarity	NPC477355
0.8411	Intermediate Similarity	NPC87090
0.8407	Intermediate Similarity	NPC477103
0.8407	Intermediate Similarity	NPC50223
0.8376	Intermediate Similarity	NPC475130
0.8376	Intermediate Similarity	NPC474286
0.8364	Intermediate Similarity	NPC472755
0.8333	Intermediate Similarity	NPC287311
0.8333	Intermediate Similarity	NPC470188
0.8319	Intermediate Similarity	NPC59489
0.8319	Intermediate Similarity	NPC477102
0.8319	Intermediate Similarity	NPC139838
0.8318	Intermediate Similarity	NPC477354
0.8304	Intermediate Similarity	NPC477513
0.8273	Intermediate Similarity	NPC472754
0.8261	Intermediate Similarity	NPC471933
0.8246	Intermediate Similarity	NPC41551
0.8246	Intermediate Similarity	NPC257240
0.823	Intermediate Similarity	NPC117604
0.8214	Intermediate Similarity	NPC54737
0.8211	Intermediate Similarity	NPC236999
0.819	Intermediate Similarity	NPC101400
0.819	Intermediate Similarity	NPC101965
0.8182	Intermediate Similarity	NPC472753
0.8182	Intermediate Similarity	NPC201718
0.8158	Intermediate Similarity	NPC77089
0.8145	Intermediate Similarity	NPC13071
0.8142	Intermediate Similarity	NPC26617
0.8136	Intermediate Similarity	NPC239273
0.8125	Intermediate Similarity	NPC472756
0.8125	Intermediate Similarity	NPC474741
0.812	Intermediate Similarity	NPC138303
0.812	Intermediate Similarity	NPC133677
0.812	Intermediate Similarity	NPC67290
0.8103	Intermediate Similarity	NPC313921
0.8103	Intermediate Similarity	NPC98038
0.8095	Intermediate Similarity	NPC58029
0.807	Intermediate Similarity	NPC169888
0.807	Intermediate Similarity	NPC55972
0.807	Intermediate Similarity	NPC308191
0.807	Intermediate Similarity	NPC327286
0.8053	Intermediate Similarity	NPC314244
0.8053	Intermediate Similarity	NPC44004
0.8037	Intermediate Similarity	NPC477361
0.8037	Intermediate Similarity	NPC202824
0.8036	Intermediate Similarity	NPC475871
0.8036	Intermediate Similarity	NPC475945
0.8036	Intermediate Similarity	NPC123505
0.8034	Intermediate Similarity	NPC106395
0.8034	Intermediate Similarity	NPC46269
0.8033	Intermediate Similarity	NPC472399
0.8031	Intermediate Similarity	NPC471234
0.8018	Intermediate Similarity	NPC474339
0.8018	Intermediate Similarity	NPC171759
0.8018	Intermediate Similarity	NPC476270
0.8018	Intermediate Similarity	NPC477950
0.8018	Intermediate Similarity	NPC264477
0.8018	Intermediate Similarity	NPC164598
0.8018	Intermediate Similarity	NPC477511
0.8016	Intermediate Similarity	NPC34963
0.8	Intermediate Similarity	NPC15218
0.8	Intermediate Similarity	NPC471934
0.8	Intermediate Similarity	NPC109556
0.8	Intermediate Similarity	NPC35109
0.7982	Intermediate Similarity	NPC194620
0.7982	Intermediate Similarity	NPC72813
0.7982	Intermediate Similarity	NPC326994
0.7982	Intermediate Similarity	NPC474421
0.7982	Intermediate Similarity	NPC476315
0.7982	Intermediate Similarity	NPC324327
0.7967	Intermediate Similarity	NPC144625
0.7966	Intermediate Similarity	NPC265290
0.7966	Intermediate Similarity	NPC305044
0.7965	Intermediate Similarity	NPC169843
0.7953	Intermediate Similarity	NPC469674
0.7953	Intermediate Similarity	NPC224623
0.7953	Intermediate Similarity	NPC469673
0.7951	Intermediate Similarity	NPC19464
0.7949	Intermediate Similarity	NPC76550
0.7949	Intermediate Similarity	NPC317687
0.7949	Intermediate Similarity	NPC138757
0.7949	Intermediate Similarity	NPC170487
0.7949	Intermediate Similarity	NPC123855
0.7946	Intermediate Similarity	NPC149371
0.7946	Intermediate Similarity	NPC474747
0.7946	Intermediate Similarity	NPC471148
0.7944	Intermediate Similarity	NPC221282
0.7937	Intermediate Similarity	NPC196921
0.7937	Intermediate Similarity	NPC241935
0.7937	Intermediate Similarity	NPC279478
0.7937	Intermediate Similarity	NPC220757
0.7928	Intermediate Similarity	NPC280963
0.7928	Intermediate Similarity	NPC288876
0.7928	Intermediate Similarity	NPC475949
0.792	Intermediate Similarity	NPC172823
0.7917	Intermediate Similarity	NPC118638
0.7913	Intermediate Similarity	NPC233379
0.7913	Intermediate Similarity	NPC14862
0.7913	Intermediate Similarity	NPC474664
0.7899	Intermediate Similarity	NPC148458
0.7895	Intermediate Similarity	NPC291643
0.7895	Intermediate Similarity	NPC9303
0.7895	Intermediate Similarity	NPC16313
0.7895	Intermediate Similarity	NPC223450
0.7895	Intermediate Similarity	NPC179891
0.7895	Intermediate Similarity	NPC475802
0.7895	Intermediate Similarity	NPC243998
0.7895	Intermediate Similarity	NPC474101
0.7891	Intermediate Similarity	NPC476823
0.7886	Intermediate Similarity	NPC1538
0.7886	Intermediate Similarity	NPC42747
0.7886	Intermediate Similarity	NPC473802
0.787	Intermediate Similarity	NPC125180
0.7869	Intermediate Similarity	NPC472001
0.7869	Intermediate Similarity	NPC471999
0.7869	Intermediate Similarity	NPC472401
0.7869	Intermediate Similarity	NPC52839
0.7869	Intermediate Similarity	NPC472000
0.7863	Intermediate Similarity	NPC474750
0.7863	Intermediate Similarity	NPC214797
0.7863	Intermediate Similarity	NPC231589
0.7863	Intermediate Similarity	NPC118860
0.7863	Intermediate Similarity	NPC317107
0.7857	Intermediate Similarity	NPC47880
0.7857	Intermediate Similarity	NPC474742
0.7857	Intermediate Similarity	NPC470880
0.7851	Intermediate Similarity	NPC472667
0.7845	Intermediate Similarity	NPC475922
0.7838	Intermediate Similarity	NPC471144
0.7838	Intermediate Similarity	NPC161855
0.7833	Intermediate Similarity	NPC471146
0.7826	Intermediate Similarity	NPC473911
0.7823	Intermediate Similarity	NPC473919
0.7823	Intermediate Similarity	NPC473709
0.7818	Intermediate Similarity	NPC17585
0.7818	Intermediate Similarity	NPC473859
0.7807	Intermediate Similarity	NPC471143
0.7807	Intermediate Similarity	NPC477510
0.7807	Intermediate Similarity	NPC203659
0.7807	Intermediate Similarity	NPC472748
0.7807	Intermediate Similarity	NPC100487
0.7805	Intermediate Similarity	NPC192309
0.7805	Intermediate Similarity	NPC162009
0.7805	Intermediate Similarity	NPC107493
0.7805	Intermediate Similarity	NPC257017
0.7803	Intermediate Similarity	NPC25887
0.7797	Intermediate Similarity	NPC221144
0.7797	Intermediate Similarity	NPC475524
0.7797	Intermediate Similarity	NPC100267
0.7795	Intermediate Similarity	NPC213634
0.7795	Intermediate Similarity	NPC469351
0.7788	Intermediate Similarity	NPC320019
0.7788	Intermediate Similarity	NPC324017
0.7787	Intermediate Similarity	NPC145182
0.7787	Intermediate Similarity	NPC471128
0.7787	Intermediate Similarity	NPC79579
0.7787	Intermediate Similarity	NPC471126
0.7787	Intermediate Similarity	NPC157252
0.7778	Intermediate Similarity	NPC161816
0.7778	Intermediate Similarity	NPC20713
0.7778	Intermediate Similarity	NPC115257
0.7768	Intermediate Similarity	NPC471381
0.7768	Intermediate Similarity	NPC477512
0.7768	Intermediate Similarity	NPC186861
0.776	Intermediate Similarity	NPC471939
0.776	Intermediate Similarity	NPC15095
0.776	Intermediate Similarity	NPC473635
0.7759	Intermediate Similarity	NPC322903
0.775	Intermediate Similarity	NPC476710
0.775	Intermediate Similarity	NPC270958
0.775	Intermediate Similarity	NPC255450
0.775	Intermediate Similarity	NPC170692
0.775	Intermediate Similarity	NPC476711
0.7748	Intermediate Similarity	NPC161493
0.7748	Intermediate Similarity	NPC108475
0.7748	Intermediate Similarity	NPC471140
0.7748	Intermediate Similarity	NPC170143
0.7748	Intermediate Similarity	NPC477949
0.7748	Intermediate Similarity	NPC213947
0.7742	Intermediate Similarity	NPC469789
0.7739	Intermediate Similarity	NPC472749
0.7739	Intermediate Similarity	NPC470975
0.7739	Intermediate Similarity	NPC103088
0.7739	Intermediate Similarity	NPC470979
0.7739	Intermediate Similarity	NPC472751

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 NPC475305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	2401
0.2-0.3	3802
0.3-0.4	1735
0.4-0.5	562
0.5-0.6	226
0.6-0.7	127
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8246	Intermediate Similarity	NPD6371	Approved
0.8142	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6319	Approved
0.7523	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7402	Intermediate Similarity	NPD7492	Approved
0.7364	Intermediate Similarity	NPD6698	Approved
0.7364	Intermediate Similarity	NPD7736	Approved
0.7364	Intermediate Similarity	NPD46	Approved
0.736	Intermediate Similarity	NPD6054	Approved
0.7344	Intermediate Similarity	NPD6616	Approved
0.7287	Intermediate Similarity	NPD8293	Discontinued
0.7287	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD6649	Approved
0.7258	Intermediate Similarity	NPD7115	Discovery
0.7257	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6373	Approved
0.725	Intermediate Similarity	NPD6372	Approved
0.7244	Intermediate Similarity	NPD6370	Approved
0.7222	Intermediate Similarity	NPD6059	Approved
0.7213	Intermediate Similarity	NPD6053	Discontinued
0.7207	Intermediate Similarity	NPD7838	Discovery
0.7188	Intermediate Similarity	NPD7604	Phase 2
0.7167	Intermediate Similarity	NPD6899	Approved
0.7167	Intermediate Similarity	NPD6881	Approved
0.7165	Intermediate Similarity	NPD6015	Approved
0.7165	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7131	Intermediate Similarity	NPD8130	Phase 1
0.7109	Intermediate Similarity	NPD5988	Approved
0.7083	Intermediate Similarity	NPD5697	Approved
0.7073	Intermediate Similarity	NPD6882	Approved
0.7064	Intermediate Similarity	NPD5363	Approved
0.7049	Intermediate Similarity	NPD7102	Approved
0.7049	Intermediate Similarity	NPD7290	Approved
0.7049	Intermediate Similarity	NPD6883	Approved
0.7045	Intermediate Similarity	NPD7319	Approved
0.7025	Intermediate Similarity	NPD7320	Approved
0.7016	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD5786	Approved
0.6992	Remote Similarity	NPD6617	Approved
0.6992	Remote Similarity	NPD6847	Approved
0.6992	Remote Similarity	NPD6869	Approved
0.6984	Remote Similarity	NPD6009	Approved
0.6983	Remote Similarity	NPD6083	Phase 2
0.6983	Remote Similarity	NPD6084	Phase 2
0.6967	Remote Similarity	NPD6014	Approved
0.6967	Remote Similarity	NPD6012	Approved
0.6967	Remote Similarity	NPD6013	Approved
0.6964	Remote Similarity	NPD1695	Approved
0.6947	Remote Similarity	NPD7507	Approved
0.6944	Remote Similarity	NPD6435	Approved
0.6942	Remote Similarity	NPD5701	Approved
0.6911	Remote Similarity	NPD4634	Approved
0.6909	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5983	Phase 2
0.6885	Remote Similarity	NPD6686	Approved
0.6885	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD5282	Discontinued
0.686	Remote Similarity	NPD6008	Approved
0.6852	Remote Similarity	NPD5369	Approved
0.6818	Remote Similarity	NPD6336	Discontinued
0.681	Remote Similarity	NPD5695	Phase 3
0.6789	Remote Similarity	NPD4269	Approved
0.6789	Remote Similarity	NPD4270	Approved
0.678	Remote Similarity	NPD5696	Approved
0.6759	Remote Similarity	NPD5368	Approved
0.672	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6033	Approved
0.6691	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD5344	Discontinued
0.6641	Remote Similarity	NPD8033	Approved
0.6641	Remote Similarity	NPD6274	Approved
0.664	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7638	Approved
0.6639	Remote Similarity	NPD4225	Approved
0.6639	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4250	Approved
0.6637	Remote Similarity	NPD4251	Approved
0.6615	Remote Similarity	NPD7101	Approved
0.6615	Remote Similarity	NPD7100	Approved
0.6613	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4252	Approved
0.6606	Remote Similarity	NPD4819	Approved
0.6606	Remote Similarity	NPD4821	Approved
0.6606	Remote Similarity	NPD4822	Approved
0.6606	Remote Similarity	NPD4820	Approved
0.6583	Remote Similarity	NPD7639	Approved
0.6583	Remote Similarity	NPD5285	Approved
0.6583	Remote Similarity	NPD5286	Approved
0.6583	Remote Similarity	NPD4696	Approved
0.6583	Remote Similarity	NPD7640	Approved
0.6577	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4755	Approved
0.6552	Remote Similarity	NPD5693	Phase 1
0.6549	Remote Similarity	NPD4249	Approved
0.6541	Remote Similarity	NPD7642	Approved
0.6538	Remote Similarity	NPD6335	Approved
0.6532	Remote Similarity	NPD6412	Phase 2
0.6515	Remote Similarity	NPD8513	Phase 3
0.6515	Remote Similarity	NPD8515	Approved
0.6515	Remote Similarity	NPD8516	Approved
0.6515	Remote Similarity	NPD8517	Approved
0.6504	Remote Similarity	NPD5141	Approved
0.6504	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5956	Approved
0.6496	Remote Similarity	NPD5778	Approved
0.6496	Remote Similarity	NPD5779	Approved
0.6486	Remote Similarity	NPD5209	Approved
0.6475	Remote Similarity	NPD4633	Approved
0.6475	Remote Similarity	NPD5225	Approved
0.6475	Remote Similarity	NPD5224	Approved
0.6475	Remote Similarity	NPD5226	Approved
0.6462	Remote Similarity	NPD6317	Approved
0.6446	Remote Similarity	NPD6648	Approved
0.6446	Remote Similarity	NPD4700	Approved
0.6439	Remote Similarity	NPD8377	Approved
0.6439	Remote Similarity	NPD8294	Approved
0.6429	Remote Similarity	NPD7154	Phase 3
0.6423	Remote Similarity	NPD5174	Approved
0.6423	Remote Similarity	NPD5175	Approved
0.6422	Remote Similarity	NPD4268	Approved
0.6422	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4271	Approved
0.6418	Remote Similarity	NPD7829	Approved
0.6418	Remote Similarity	NPD7830	Approved
0.6412	Remote Similarity	NPD6313	Approved
0.6412	Remote Similarity	NPD7328	Approved
0.6412	Remote Similarity	NPD6314	Approved
0.6412	Remote Similarity	NPD7327	Approved
0.641	Remote Similarity	NPD7637	Suspended
0.6403	Remote Similarity	NPD6845	Suspended
0.64	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5223	Approved
0.6393	Remote Similarity	NPD1700	Approved
0.6391	Remote Similarity	NPD8380	Approved
0.6391	Remote Similarity	NPD8335	Approved
0.6391	Remote Similarity	NPD7503	Approved
0.6391	Remote Similarity	NPD8296	Approved
0.6391	Remote Similarity	NPD8378	Approved
0.6391	Remote Similarity	NPD6909	Approved
0.6391	Remote Similarity	NPD6908	Approved
0.6391	Remote Similarity	NPD8379	Approved
0.6387	Remote Similarity	NPD4629	Approved
0.6387	Remote Similarity	NPD5210	Approved
0.6379	Remote Similarity	NPD4753	Phase 2
0.6379	Remote Similarity	NPD6080	Approved
0.6379	Remote Similarity	NPD6673	Approved
0.6379	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6356	Remote Similarity	NPD6399	Phase 3
0.6349	Remote Similarity	NPD4730	Approved
0.6349	Remote Similarity	NPD4729	Approved
0.6339	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7839	Suspended
0.632	Remote Similarity	NPD4767	Approved
0.632	Remote Similarity	NPD4768	Approved
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.6277	Remote Similarity	NPD8074	Phase 3
0.6271	Remote Similarity	NPD6050	Approved
0.6271	Remote Similarity	NPD6411	Approved
0.6269	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5247	Approved
0.6241	Remote Similarity	NPD4522	Approved
0.6231	Remote Similarity	NPD8133	Approved
0.6222	Remote Similarity	NPD8080	Discontinued
0.622	Remote Similarity	NPD5128	Approved
0.6196	Remote Similarity	NPD7799	Discontinued
0.6186	Remote Similarity	NPD5692	Phase 3
0.616	Remote Similarity	NPD4754	Approved
0.6148	Remote Similarity	NPD6921	Approved
0.614	Remote Similarity	NPD6110	Phase 1
0.614	Remote Similarity	NPD5331	Approved
0.614	Remote Similarity	NPD5332	Approved
0.6136	Remote Similarity	NPD6868	Approved
0.6134	Remote Similarity	NPD5284	Approved
0.6134	Remote Similarity	NPD5694	Approved
0.6134	Remote Similarity	NPD5281	Approved
0.6121	Remote Similarity	NPD5330	Approved
0.6121	Remote Similarity	NPD7146	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