NPASS Compound

Structure

NPC472188 OpenBabel07101718232D 36 38 0 0 1 0 0 0 0 0999 V2000 6.7567 -1.0549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2037 -3.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7823 -2.7426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 -3.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7031 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6238 2.9971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3464 -1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 -0.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0013 -0.3686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7823 -1.0549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3599 -4.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3208 -1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8336 -1.0549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3278 -2.5165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 -2.5165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2951 -1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 -3.9780 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8592 -0.0806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9719 2.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1716 -3.0036 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3278 -1.5421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 -1.5421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1716 -0.0806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3278 -4.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 -0.8901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9690 -0.1018 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8592 -1.0549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1716 -1.0549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0188 2.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3278 -5.4395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3278 0.4066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3494 -1.0927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2730 1.3463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1716 -3.9780 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 10 2 0 0 0 0 2 11 1 0 0 0 0 3 17 2 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 28 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 22 2 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 18 25 1 0 0 0 0 19 28 1 1 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 35 1 1 0 0 0 22 26 1 0 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 29 1 1 0 0 0 24 32 1 0 0 0 0 25 31 2 0 0 0 0 25 35 1 0 0 0 0 26 33 1 1 0 0 0 26 36 1 0 0 0 0 27 29 1 1 0 0 0 27 34 1 0 0 0 0 27 36 1 0 0 0 0 28 7 1 6 0 0 0 29 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.31
Volume:	532.82
LogP:	4.451
LogD:	3.945
LogS:	-5.135
# Rotatable Bonds:	12
TPSA:	80.29
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	5.868
Fsp3:	0.724
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:	-4.713
MDCK Permeability:	2.410916204098612e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	78.87052154541016%
Volume Distribution (VD):	2.383
Pgp-substrate:	17.206972122192383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.202
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	4.628
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.525
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.864
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.762
Carcinogencity:	0.563
Eye Corrosion:	0.015
Eye Irritation:	0.035
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC472188

Natural Product ID:	NPC472188
*Common Name:**	XDGNGAAYVBELLQ-PJJSSYIVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XDGNGAAYVBELLQ-PJJSSYIVSA-N
Standard InCHI:	InChI=1S/C29H44O7/c1-10-17(3)12-13-28(7)19(5)14-24(32-8)29-22(26(33-9)36-27(29)34-20(6)30)15-21(16-23(28)29)35-25(31)18(4)11-2/h10,15,18-19,21,23-24,26-27H,1,3,11-14,16H2,2,4-9H3/t18?,19-,21+,23+,24+,26+,27-,28-,29-/m1/s1
SMILES:	C=CC(=C)CC[C@]1(C)[C@H](C)C[C@@H]([C@@]23[C@H]1C[C@@H](OC(=O)C(CC)C)C=C3[C@H](O[C@H]2OC(=O)C)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3343971
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]

☑ 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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	=	4.0	ug.mL-1	PMID[549983]

☑ 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 NPC472188 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	216
0.1-0.2	1156
0.2-0.3	4313
0.3-0.4	9039
0.4-0.5	12935
0.5-0.6	7343
0.6-0.7	6314
0.7-0.8	1245
0.8-0.85	41
0.85-0.9	27
0.9-0.95	46
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC471366
0.989	High Similarity	NPC476800
0.989	High Similarity	NPC472186
0.989	High Similarity	NPC318917
0.9783	High Similarity	NPC472187
0.9783	High Similarity	NPC473545
0.9783	High Similarity	NPC473204
0.9778	High Similarity	NPC471362
0.9778	High Similarity	NPC471372
0.9778	High Similarity	NPC472189
0.967	High Similarity	NPC171598
0.9574	High Similarity	NPC471363
0.9574	High Similarity	NPC238397
0.9474	High Similarity	NPC7613
0.9474	High Similarity	NPC7644
0.9474	High Similarity	NPC475889
0.9474	High Similarity	NPC127933
0.9474	High Similarity	NPC134270
0.9451	High Similarity	NPC88507
0.9375	High Similarity	NPC470321
0.9375	High Similarity	NPC264867
0.9375	High Similarity	NPC201880
0.9375	High Similarity	NPC473207
0.9375	High Similarity	NPC81567
0.9278	High Similarity	NPC252296
0.9247	High Similarity	NPC311166
0.9184	High Similarity	NPC125423
0.9184	High Similarity	NPC184512
0.9184	High Similarity	NPC88013
0.9091	High Similarity	NPC128795
0.9091	High Similarity	NPC135015
0.9091	High Similarity	NPC217921
0.9091	High Similarity	NPC311223
0.9091	High Similarity	NPC48548
0.9043	High Similarity	NPC94905
0.9043	High Similarity	NPC8954
0.9	High Similarity	NPC40728
0.9	High Similarity	NPC316974
0.8911	High Similarity	NPC119550
0.8878	High Similarity	NPC132395
0.8878	High Similarity	NPC471364
0.8878	High Similarity	NPC471365
0.88	High Similarity	NPC109376
0.875	High Similarity	NPC98112
0.8713	High Similarity	NPC224660
0.8713	High Similarity	NPC470024
0.87	High Similarity	NPC218158
0.87	High Similarity	NPC172867
0.8571	High Similarity	NPC161527
0.8571	High Similarity	NPC228251
0.8571	High Similarity	NPC477968
0.8571	High Similarity	NPC20113
0.8571	High Similarity	NPC477971
0.8571	High Similarity	NPC477972
0.8571	High Similarity	NPC219285
0.8544	High Similarity	NPC316708
0.85	High Similarity	NPC120009
0.8495	Intermediate Similarity	NPC69713
0.8462	Intermediate Similarity	NPC17791
0.8462	Intermediate Similarity	NPC470026
0.8462	Intermediate Similarity	NPC471367
0.8447	Intermediate Similarity	NPC112457
0.8404	Intermediate Similarity	NPC470819
0.8404	Intermediate Similarity	NPC293044
0.8387	Intermediate Similarity	NPC102640
0.8381	Intermediate Similarity	NPC328074
0.8381	Intermediate Similarity	NPC470025
0.8381	Intermediate Similarity	NPC321272
0.8381	Intermediate Similarity	NPC317460
0.8316	Intermediate Similarity	NPC470817
0.8316	Intermediate Similarity	NPC471370
0.8316	Intermediate Similarity	NPC471371
0.8302	Intermediate Similarity	NPC470027
0.8298	Intermediate Similarity	NPC477128
0.8283	Intermediate Similarity	NPC473154
0.828	Intermediate Similarity	NPC471369
0.828	Intermediate Similarity	NPC471368
0.828	Intermediate Similarity	NPC102996
0.8235	Intermediate Similarity	NPC222161
0.8229	Intermediate Similarity	NPC477574
0.8229	Intermediate Similarity	NPC474631
0.82	Intermediate Similarity	NPC473219
0.82	Intermediate Similarity	NPC470761
0.8163	Intermediate Similarity	NPC135224
0.8163	Intermediate Similarity	NPC477969
0.8163	Intermediate Similarity	NPC100892
0.8163	Intermediate Similarity	NPC477970
0.8144	Intermediate Similarity	NPC99653
0.8131	Intermediate Similarity	NPC157441
0.8125	Intermediate Similarity	NPC469403
0.8105	Intermediate Similarity	NPC263079
0.81	Intermediate Similarity	NPC474440
0.8095	Intermediate Similarity	NPC206618
0.8085	Intermediate Similarity	NPC118266
0.8085	Intermediate Similarity	NPC323209
0.8081	Intermediate Similarity	NPC73858
0.8081	Intermediate Similarity	NPC165632
0.8081	Intermediate Similarity	NPC112654
0.8077	Intermediate Similarity	NPC475074
0.8077	Intermediate Similarity	NPC293512
0.8061	Intermediate Similarity	NPC477722
0.8061	Intermediate Similarity	NPC477130
0.8061	Intermediate Similarity	NPC189513
0.8061	Intermediate Similarity	NPC477129
0.8041	Intermediate Similarity	NPC65513
0.8041	Intermediate Similarity	NPC124374
0.8037	Intermediate Similarity	NPC194951
0.8037	Intermediate Similarity	NPC12046
0.8022	Intermediate Similarity	NPC469802
0.8022	Intermediate Similarity	NPC473685
0.8021	Intermediate Similarity	NPC246028
0.8021	Intermediate Similarity	NPC261320
0.802	Intermediate Similarity	NPC324841
0.8	Intermediate Similarity	NPC239547
0.8	Intermediate Similarity	NPC309503
0.8	Intermediate Similarity	NPC155319
0.8	Intermediate Similarity	NPC38948
0.8	Intermediate Similarity	NPC125551
0.8	Intermediate Similarity	NPC91197
0.8	Intermediate Similarity	NPC96597
0.8	Intermediate Similarity	NPC100912
0.7981	Intermediate Similarity	NPC82251
0.7981	Intermediate Similarity	NPC239961
0.798	Intermediate Similarity	NPC37603
0.798	Intermediate Similarity	NPC471786
0.798	Intermediate Similarity	NPC275310
0.798	Intermediate Similarity	NPC286612
0.798	Intermediate Similarity	NPC230347
0.7979	Intermediate Similarity	NPC472442
0.7963	Intermediate Similarity	NPC264153
0.7963	Intermediate Similarity	NPC474410
0.7963	Intermediate Similarity	NPC293658
0.7961	Intermediate Similarity	NPC471887
0.7961	Intermediate Similarity	NPC471450
0.7961	Intermediate Similarity	NPC471885
0.7961	Intermediate Similarity	NPC471888
0.7961	Intermediate Similarity	NPC45897
0.7961	Intermediate Similarity	NPC254202
0.7961	Intermediate Similarity	NPC471886
0.7961	Intermediate Similarity	NPC23584
0.7959	Intermediate Similarity	NPC12297
0.7959	Intermediate Similarity	NPC163902
0.7957	Intermediate Similarity	NPC472440
0.7946	Intermediate Similarity	NPC204731
0.7941	Intermediate Similarity	NPC280991
0.7941	Intermediate Similarity	NPC198992
0.7938	Intermediate Similarity	NPC220216
0.7938	Intermediate Similarity	NPC48732
0.7935	Intermediate Similarity	NPC25554
0.7928	Intermediate Similarity	NPC122971
0.7921	Intermediate Similarity	NPC107806
0.7921	Intermediate Similarity	NPC216478
0.7921	Intermediate Similarity	NPC72647
0.7917	Intermediate Similarity	NPC473879
0.7917	Intermediate Similarity	NPC106332
0.7909	Intermediate Similarity	NPC23046
0.7905	Intermediate Similarity	NPC472390
0.79	Intermediate Similarity	NPC209297
0.79	Intermediate Similarity	NPC475380
0.7885	Intermediate Similarity	NPC470768
0.7885	Intermediate Similarity	NPC476764
0.7885	Intermediate Similarity	NPC476763
0.7879	Intermediate Similarity	NPC140277
0.7879	Intermediate Similarity	NPC473434
0.7879	Intermediate Similarity	NPC471446
0.7879	Intermediate Similarity	NPC474841
0.787	Intermediate Similarity	NPC473125
0.787	Intermediate Similarity	NPC222834
0.7864	Intermediate Similarity	NPC300399
0.7864	Intermediate Similarity	NPC471482
0.7864	Intermediate Similarity	NPC472552
0.7864	Intermediate Similarity	NPC471889
0.7864	Intermediate Similarity	NPC470571
0.7864	Intermediate Similarity	NPC469606
0.7864	Intermediate Similarity	NPC273005
0.7864	Intermediate Similarity	NPC31058
0.7864	Intermediate Similarity	NPC37207
0.7864	Intermediate Similarity	NPC11956
0.7857	Intermediate Similarity	NPC473944
0.785	Intermediate Similarity	NPC83005
0.7849	Intermediate Similarity	NPC471218
0.7838	Intermediate Similarity	NPC473617
0.7838	Intermediate Similarity	NPC473828
0.783	Intermediate Similarity	NPC325054
0.7822	Intermediate Similarity	NPC311241
0.7822	Intermediate Similarity	NPC257726
0.7822	Intermediate Similarity	NPC475446
0.7822	Intermediate Similarity	NPC110937
0.7822	Intermediate Similarity	NPC204054
0.7812	Intermediate Similarity	NPC471779
0.7812	Intermediate Similarity	NPC166857
0.781	Intermediate Similarity	NPC476760
0.781	Intermediate Similarity	NPC476761
0.781	Intermediate Similarity	NPC127609
0.781	Intermediate Similarity	NPC469607
0.781	Intermediate Similarity	NPC470763
0.781	Intermediate Similarity	NPC476762
0.781	Intermediate Similarity	NPC470767
0.7807	Intermediate Similarity	NPC41129
0.78	Intermediate Similarity	NPC13924

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 NPC472188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1378
0.2-0.3	3876
0.3-0.4	2414
0.4-0.5	835
0.5-0.6	283
0.6-0.7	180
0.7-0.8	8
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
0.7573	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.7328	Intermediate Similarity	NPD7503	Approved
0.7245	Intermediate Similarity	NPD1694	Approved
0.7238	Intermediate Similarity	NPD4225	Approved
0.7217	Intermediate Similarity	NPD7328	Approved
0.7217	Intermediate Similarity	NPD7327	Approved
0.7179	Intermediate Similarity	NPD8513	Phase 3
0.7179	Intermediate Similarity	NPD8516	Approved
0.7179	Intermediate Similarity	NPD8515	Approved
0.7179	Intermediate Similarity	NPD8517	Approved
0.7179	Intermediate Similarity	NPD8033	Approved
0.7155	Intermediate Similarity	NPD7516	Approved
0.7094	Intermediate Similarity	NPD8294	Approved
0.7094	Intermediate Similarity	NPD8377	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7034	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD8378	Approved
0.7034	Intermediate Similarity	NPD8296	Approved
0.7034	Intermediate Similarity	NPD8380	Approved
0.7034	Intermediate Similarity	NPD8335	Approved
0.7009	Intermediate Similarity	NPD6648	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.699	Remote Similarity	NPD7637	Suspended
0.697	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6051	Approved
0.6939	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD5779	Approved
0.6923	Remote Similarity	NPD5778	Approved
0.6911	Remote Similarity	NPD7319	Approved
0.6881	Remote Similarity	NPD7632	Discontinued
0.687	Remote Similarity	NPD8133	Approved
0.6857	Remote Similarity	NPD7900	Approved
0.6857	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6370	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6814	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5344	Discontinued
0.6783	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8293	Discontinued
0.6737	Remote Similarity	NPD8039	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD7748	Approved
0.6695	Remote Similarity	NPD7115	Discovery
0.6695	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6613	Remote Similarity	NPD7078	Approved
0.6613	Remote Similarity	NPD8074	Phase 3
0.6579	Remote Similarity	NPD6881	Approved
0.6579	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD7838	Discovery
0.6555	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5739	Approved
0.6549	Remote Similarity	NPD6675	Approved
0.6549	Remote Similarity	NPD6402	Approved
0.6549	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5737	Approved
0.6538	Remote Similarity	NPD6903	Approved
0.6538	Remote Similarity	NPD6672	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.6509	Remote Similarity	NPD7515	Phase 2
0.6504	Remote Similarity	NPD6067	Discontinued
0.6496	Remote Similarity	NPD6053	Discontinued
0.6491	Remote Similarity	NPD5697	Approved
0.6481	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6101	Approved
0.6475	Remote Similarity	NPD6016	Approved
0.6475	Remote Similarity	NPD6015	Approved
0.6471	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6466	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD4251	Approved
0.6442	Remote Similarity	NPD3573	Approved
0.6442	Remote Similarity	NPD4250	Approved
0.6435	Remote Similarity	NPD7320	Approved
0.6435	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5988	Approved
0.6415	Remote Similarity	NPD6698	Approved
0.6415	Remote Similarity	NPD46	Approved
0.641	Remote Similarity	NPD8130	Phase 1
0.641	Remote Similarity	NPD6869	Approved
0.641	Remote Similarity	NPD6617	Approved
0.641	Remote Similarity	NPD6649	Approved
0.641	Remote Similarity	NPD6650	Approved
0.641	Remote Similarity	NPD6847	Approved
0.6379	Remote Similarity	NPD6014	Approved
0.6379	Remote Similarity	NPD6012	Approved
0.6379	Remote Similarity	NPD6373	Approved
0.6379	Remote Similarity	NPD6013	Approved
0.6379	Remote Similarity	NPD6372	Approved
0.6374	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6695	Phase 3
0.6356	Remote Similarity	NPD8297	Approved
0.6355	Remote Similarity	NPD5693	Phase 1
0.6355	Remote Similarity	NPD8035	Phase 2
0.6355	Remote Similarity	NPD8034	Phase 2
0.6348	Remote Similarity	NPD5701	Approved
0.6346	Remote Similarity	NPD4249	Approved
0.6321	Remote Similarity	NPD1695	Approved
0.6311	Remote Similarity	NPD4786	Approved
0.6311	Remote Similarity	NPD3668	Phase 3
0.6303	Remote Similarity	NPD4632	Approved
0.63	Remote Similarity	NPD7645	Phase 2
0.6293	Remote Similarity	NPD6011	Approved
0.6275	Remote Similarity	NPD5209	Approved
0.6275	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD5207	Approved
0.626	Remote Similarity	NPD6319	Approved
0.6238	Remote Similarity	NPD7525	Registered
0.6238	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD8264	Approved
0.6216	Remote Similarity	NPD6083	Phase 2
0.6216	Remote Similarity	NPD6084	Phase 2
0.6204	Remote Similarity	NPD6079	Approved
0.6204	Remote Similarity	NPD6050	Approved
0.6204	Remote Similarity	NPD5694	Approved
0.6204	Remote Similarity	NPD7983	Approved
0.619	Remote Similarity	NPD6098	Approved
0.619	Remote Similarity	NPD3618	Phase 1
0.6182	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5695	Phase 3
0.6168	Remote Similarity	NPD6080	Approved
0.6168	Remote Similarity	NPD6904	Approved
0.6168	Remote Similarity	NPD5328	Approved
0.6168	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.614	Remote Similarity	NPD5211	Phase 2
0.6139	Remote Similarity	NPD6929	Approved
0.6134	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7750	Discontinued
0.6132	Remote Similarity	NPD7524	Approved
0.6126	Remote Similarity	NPD7839	Suspended
0.6111	Remote Similarity	NPD5692	Phase 3
0.6111	Remote Similarity	NPD7604	Phase 2
0.6111	Remote Similarity	NPD3168	Discontinued
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6095	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6001	Approved
0.6091	Remote Similarity	NPD5282	Discontinued
0.608	Remote Similarity	NPD5983	Phase 2
0.6078	Remote Similarity	NPD4821	Approved
0.6078	Remote Similarity	NPD6930	Phase 2
0.6078	Remote Similarity	NPD7514	Phase 3
0.6078	Remote Similarity	NPD4822	Approved
0.6078	Remote Similarity	NPD6931	Approved
0.6078	Remote Similarity	NPD7332	Phase 2
0.6078	Remote Similarity	NPD4820	Approved
0.6078	Remote Similarity	NPD4819	Approved
0.6071	Remote Similarity	NPD4755	Approved
0.6068	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7339	Approved
0.6061	Remote Similarity	NPD6942	Approved
0.6058	Remote Similarity	NPD7154	Phase 3
0.6055	Remote Similarity	NPD5281	Approved
0.6055	Remote Similarity	NPD5284	Approved
0.605	Remote Similarity	NPD6371	Approved
0.6048	Remote Similarity	NPD7100	Approved
0.6048	Remote Similarity	NPD7101	Approved
0.6047	Remote Similarity	NPD6033	Approved
0.604	Remote Similarity	NPD7145	Approved
0.604	Remote Similarity	NPD4271	Approved
0.604	Remote Similarity	NPD4268	Approved
0.6034	Remote Similarity	NPD5141	Approved
0.6019	Remote Similarity	NPD6902	Approved
0.6018	Remote Similarity	NPD5696	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.5982	Remote Similarity	NPD5221	Approved
0.5982	Remote Similarity	NPD5220	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data