NPASS Compound

Structure

NPC472311 OpenBabel07101718192D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 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 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 5 14 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 15 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 4 1 1 0 0 0 12 13 1 0 0 0 0 13 11 1 6 0 0 0 14 18 1 6 0 0 0 14 20 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 1 0 0 0 20 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	2.372
LogD:	1.951
LogS:	-3.477
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.813
Synthetic Accessibility Score:	5.698
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.232
MDCK Permeability:	8.563617484469432e-06
Pgp-inhibitor:	0.951
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.292

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.778
Plasma Protein Binding (PPB):	82.87928771972656%
Volume Distribution (VD):	0.466
Pgp-substrate:	13.402202606201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.489
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.189
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	2.677
Half-life (T1/2):	0.755

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.483
Drug-inuced Liver Injury (DILI):	0.27
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.097
Skin Sensitization:	0.767
Carcinogencity:	0.435
Eye Corrosion:	0.881
Eye Irritation:	0.526
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC472311

Natural Product ID:	NPC472311
*Common Name:**	ARJKNIJNDARKPR-JFMLXJOGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ARJKNIJNDARKPR-JFMLXJOGSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-18-6-3-7-19(2,17(23)24)15(18)8-16(22)20-9-12(4-5-14(18)20)13(10-20)11-21/h12-15,21H,3-11H2,1-2H3,(H,23,24)/t12-,13+,14+,15+,18+,19-,20-/m1/s1
SMILES:	CC12CCCC(C1CC(=O)C34C2CCC(C3)C(C4)CO)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358085
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:0003782] Kaurane 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
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	Root Bark	n.a.	n.a.	PMID[25338180]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	100.0	nM	PMID[455981]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	>	10000.0	nM	PMID[455981]

☑ 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 NPC472311 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	311
0.1-0.2	3134
0.2-0.3	13938
0.3-0.4	10164
0.4-0.5	6141
0.5-0.6	5355
0.6-0.7	2891
0.7-0.8	619
0.8-0.85	71
0.85-0.9	61
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC472309
0.9189	High Similarity	NPC472310
0.9079	High Similarity	NPC30583
0.9054	High Similarity	NPC185465
0.9	High Similarity	NPC476734
0.9	High Similarity	NPC469941
0.9	High Similarity	NPC252032
0.9	High Similarity	NPC319671
0.8933	High Similarity	NPC320144
0.8873	High Similarity	NPC477929
0.8873	High Similarity	NPC477850
0.8857	High Similarity	NPC470956
0.8841	High Similarity	NPC268736
0.8841	High Similarity	NPC477931
0.8784	High Similarity	NPC4209
0.8767	High Similarity	NPC477930
0.8767	High Similarity	NPC133922
0.8767	High Similarity	NPC280026
0.8767	High Similarity	NPC167702
0.875	High Similarity	NPC469940
0.8732	High Similarity	NPC64466
0.8696	High Similarity	NPC469791
0.8667	High Similarity	NPC180199
0.8667	High Similarity	NPC477919
0.8667	High Similarity	NPC477918
0.8667	High Similarity	NPC207010
0.8667	High Similarity	NPC317913
0.8649	High Similarity	NPC212733
0.8649	High Similarity	NPC132064
0.8611	High Similarity	NPC108131
0.859	High Similarity	NPC61107
0.859	High Similarity	NPC289486
0.8571	High Similarity	NPC42060
0.8553	High Similarity	NPC34046
0.8553	High Similarity	NPC80089
0.8553	High Similarity	NPC199965
0.8553	High Similarity	NPC224802
0.8553	High Similarity	NPC171426
0.8553	High Similarity	NPC476732
0.8553	High Similarity	NPC324700
0.8533	High Similarity	NPC477933
0.8533	High Similarity	NPC477932
0.8493	Intermediate Similarity	NPC320549
0.8493	Intermediate Similarity	NPC58057
0.8493	Intermediate Similarity	NPC473267
0.8493	Intermediate Similarity	NPC151018
0.8493	Intermediate Similarity	NPC156277
0.8472	Intermediate Similarity	NPC196197
0.8472	Intermediate Similarity	NPC324607
0.8472	Intermediate Similarity	NPC474962
0.8472	Intermediate Similarity	NPC321732
0.8472	Intermediate Similarity	NPC6120
0.8472	Intermediate Similarity	NPC327728
0.8472	Intermediate Similarity	NPC131892
0.8472	Intermediate Similarity	NPC213178
0.8451	Intermediate Similarity	NPC130459
0.8451	Intermediate Similarity	NPC474221
0.8451	Intermediate Similarity	NPC478180
0.8442	Intermediate Similarity	NPC80891
0.8442	Intermediate Similarity	NPC201276
0.8421	Intermediate Similarity	NPC169389
0.8421	Intermediate Similarity	NPC298168
0.8421	Intermediate Similarity	NPC143133
0.84	Intermediate Similarity	NPC179858
0.84	Intermediate Similarity	NPC21220
0.84	Intermediate Similarity	NPC477934
0.84	Intermediate Similarity	NPC125767
0.8378	Intermediate Similarity	NPC232112
0.8378	Intermediate Similarity	NPC310766
0.8356	Intermediate Similarity	NPC476731
0.8333	Intermediate Similarity	NPC472853
0.8333	Intermediate Similarity	NPC477851
0.8312	Intermediate Similarity	NPC329117
0.8289	Intermediate Similarity	NPC472486
0.8289	Intermediate Similarity	NPC475742
0.8289	Intermediate Similarity	NPC472487
0.8289	Intermediate Similarity	NPC5767
0.8267	Intermediate Similarity	NPC472854
0.8267	Intermediate Similarity	NPC254340
0.8243	Intermediate Similarity	NPC89310
0.8228	Intermediate Similarity	NPC12933
0.8182	Intermediate Similarity	NPC264602
0.8182	Intermediate Similarity	NPC221420
0.8182	Intermediate Similarity	NPC474404
0.8158	Intermediate Similarity	NPC195155
0.8158	Intermediate Similarity	NPC273366
0.8158	Intermediate Similarity	NPC97534
0.8158	Intermediate Similarity	NPC159789
0.8158	Intermediate Similarity	NPC174964
0.8148	Intermediate Similarity	NPC473336
0.8148	Intermediate Similarity	NPC471044
0.8125	Intermediate Similarity	NPC477935
0.8125	Intermediate Similarity	NPC121121
0.8125	Intermediate Similarity	NPC328007
0.8101	Intermediate Similarity	NPC261616
0.8082	Intermediate Similarity	NPC473225
0.8082	Intermediate Similarity	NPC474954
0.8052	Intermediate Similarity	NPC471046
0.8049	Intermediate Similarity	NPC62572
0.8049	Intermediate Similarity	NPC201655
0.8025	Intermediate Similarity	NPC259173
0.8025	Intermediate Similarity	NPC472847
0.8	Intermediate Similarity	NPC58631
0.8	Intermediate Similarity	NPC290058
0.7975	Intermediate Similarity	NPC52951
0.7952	Intermediate Similarity	NPC92139
0.7952	Intermediate Similarity	NPC472272
0.7952	Intermediate Similarity	NPC70661
0.7952	Intermediate Similarity	NPC302111
0.7949	Intermediate Similarity	NPC475031
0.7949	Intermediate Similarity	NPC23884
0.7927	Intermediate Similarity	NPC319909
0.7922	Intermediate Similarity	NPC27349
0.7922	Intermediate Similarity	NPC24014
0.7901	Intermediate Similarity	NPC477936
0.7901	Intermediate Similarity	NPC317066
0.7895	Intermediate Similarity	NPC248567
0.7875	Intermediate Similarity	NPC470609
0.7848	Intermediate Similarity	NPC26029
0.7848	Intermediate Similarity	NPC476810
0.7841	Intermediate Similarity	NPC266431
0.7838	Intermediate Similarity	NPC100917
0.7838	Intermediate Similarity	NPC180777
0.7838	Intermediate Similarity	NPC281203
0.7838	Intermediate Similarity	NPC260319
0.7838	Intermediate Similarity	NPC31187
0.7838	Intermediate Similarity	NPC2568
0.7838	Intermediate Similarity	NPC469724
0.7838	Intermediate Similarity	NPC103647
0.7821	Intermediate Similarity	NPC246445
0.7805	Intermediate Similarity	NPC327451
0.7805	Intermediate Similarity	NPC245866
0.7778	Intermediate Similarity	NPC469745
0.7765	Intermediate Similarity	NPC474719
0.7763	Intermediate Similarity	NPC126642
0.7763	Intermediate Similarity	NPC478227
0.7763	Intermediate Similarity	NPC197701
0.775	Intermediate Similarity	NPC201459
0.775	Intermediate Similarity	NPC192744
0.7738	Intermediate Similarity	NPC120395
0.7738	Intermediate Similarity	NPC80590
0.7738	Intermediate Similarity	NPC248216
0.7738	Intermediate Similarity	NPC2783
0.7733	Intermediate Similarity	NPC295788
0.7722	Intermediate Similarity	NPC471035
0.7722	Intermediate Similarity	NPC106078
0.7722	Intermediate Similarity	NPC212661
0.7722	Intermediate Similarity	NPC66105
0.7711	Intermediate Similarity	NPC50438
0.7701	Intermediate Similarity	NPC52756
0.7683	Intermediate Similarity	NPC100366
0.7683	Intermediate Similarity	NPC170985
0.7683	Intermediate Similarity	NPC242771
0.7683	Intermediate Similarity	NPC164289
0.7683	Intermediate Similarity	NPC311642
0.7683	Intermediate Similarity	NPC268040
0.7674	Intermediate Similarity	NPC200580
0.7674	Intermediate Similarity	NPC24705
0.7674	Intermediate Similarity	NPC56962
0.7662	Intermediate Similarity	NPC244708
0.7662	Intermediate Similarity	NPC177826
0.7662	Intermediate Similarity	NPC161187
0.7662	Intermediate Similarity	NPC330659
0.7654	Intermediate Similarity	NPC1882
0.7647	Intermediate Similarity	NPC252714
0.7647	Intermediate Similarity	NPC264005
0.7647	Intermediate Similarity	NPC33768
0.7647	Intermediate Similarity	NPC96496
0.7647	Intermediate Similarity	NPC269360
0.7647	Intermediate Similarity	NPC134197
0.7625	Intermediate Similarity	NPC472608
0.7619	Intermediate Similarity	NPC294438
0.7619	Intermediate Similarity	NPC264317
0.7619	Intermediate Similarity	NPC473038
0.7619	Intermediate Similarity	NPC473350
0.7614	Intermediate Similarity	NPC224060
0.7614	Intermediate Similarity	NPC476189
0.7614	Intermediate Similarity	NPC244356
0.759	Intermediate Similarity	NPC292458
0.759	Intermediate Similarity	NPC471037
0.759	Intermediate Similarity	NPC268578
0.759	Intermediate Similarity	NPC217559
0.759	Intermediate Similarity	NPC15821
0.759	Intermediate Similarity	NPC472744
0.7586	Intermediate Similarity	NPC476296
0.7586	Intermediate Similarity	NPC77756
0.7571	Intermediate Similarity	NPC476735
0.7564	Intermediate Similarity	NPC317212
0.7561	Intermediate Similarity	NPC474484
0.7561	Intermediate Similarity	NPC103754
0.7561	Intermediate Similarity	NPC476071
0.7558	Intermediate Similarity	NPC16377
0.7558	Intermediate Similarity	NPC183374
0.7558	Intermediate Similarity	NPC236459
0.7558	Intermediate Similarity	NPC211162
0.7558	Intermediate Similarity	NPC90676
0.7558	Intermediate Similarity	NPC56413
0.7556	Intermediate Similarity	NPC470387
0.7531	Intermediate Similarity	NPC31302
0.7531	Intermediate Similarity	NPC245029

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 NPC472311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	3378
0.2-0.3	3701
0.3-0.4	1048
0.4-0.5	275
0.5-0.6	233
0.6-0.7	137
0.7-0.8	12
0.8-0.85	4
0.85-0.9	18
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD6081	Approved
0.8841	High Similarity	NPD4224	Phase 2
0.8784	High Similarity	NPD6117	Approved
0.8767	High Similarity	NPD6113	Clinical (unspecified phase)
0.8696	High Similarity	NPD3171	Clinical (unspecified phase)
0.8667	High Similarity	NPD6116	Phase 1
0.8611	High Similarity	NPD4789	Approved
0.8553	High Similarity	NPD6118	Approved
0.8553	High Similarity	NPD6114	Approved
0.8553	High Similarity	NPD6697	Approved
0.8553	High Similarity	NPD6115	Approved
0.8493	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD3698	Phase 2
0.8472	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD3702	Approved
0.8356	Intermediate Similarity	NPD4245	Approved
0.8356	Intermediate Similarity	NPD4244	Approved
0.8158	Intermediate Similarity	NPD3703	Phase 2
0.8082	Intermediate Similarity	NPD5360	Phase 3
0.8082	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5777	Approved
0.7763	Intermediate Similarity	NPD4758	Discontinued
0.7625	Intermediate Similarity	NPD3671	Phase 1
0.7619	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5364	Discontinued
0.7381	Intermediate Similarity	NPD4788	Approved
0.7111	Intermediate Similarity	NPD8035	Phase 2
0.7111	Intermediate Similarity	NPD8034	Phase 2
0.7093	Intermediate Similarity	NPD4786	Approved
0.7059	Intermediate Similarity	NPD3667	Approved
0.7051	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6399	Phase 3
0.7021	Intermediate Similarity	NPD5696	Approved
0.6986	Remote Similarity	NPD3198	Approved
0.6915	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD3665	Phase 1
0.6897	Remote Similarity	NPD3666	Approved
0.6897	Remote Similarity	NPD3133	Approved
0.6889	Remote Similarity	NPD5328	Approved
0.6889	Remote Similarity	NPD4753	Phase 2
0.6882	Remote Similarity	NPD5210	Approved
0.6882	Remote Similarity	NPD4629	Approved
0.6786	Remote Similarity	NPD3617	Approved
0.6778	Remote Similarity	NPD6672	Approved
0.6778	Remote Similarity	NPD5737	Approved
0.6771	Remote Similarity	NPD8418	Phase 2
0.6761	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4787	Phase 1
0.6742	Remote Similarity	NPD3618	Phase 1
0.6739	Remote Similarity	NPD7515	Phase 2
0.6739	Remote Similarity	NPD6079	Approved
0.6702	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6632	Remote Similarity	NPD5221	Approved
0.6632	Remote Similarity	NPD5222	Approved
0.6632	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4697	Phase 3
0.6623	Remote Similarity	NPD7909	Approved
0.66	Remote Similarity	NPD5739	Approved
0.66	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD7128	Approved
0.66	Remote Similarity	NPD6675	Approved
0.6593	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4755	Approved
0.6562	Remote Similarity	NPD5173	Approved
0.6559	Remote Similarity	NPD5284	Approved
0.6559	Remote Similarity	NPD5281	Approved
0.6556	Remote Similarity	NPD7521	Approved
0.6556	Remote Similarity	NPD5279	Phase 3
0.6556	Remote Similarity	NPD7334	Approved
0.6556	Remote Similarity	NPD5330	Approved
0.6556	Remote Similarity	NPD6409	Approved
0.6556	Remote Similarity	NPD7146	Approved
0.6556	Remote Similarity	NPD6684	Approved
0.6552	Remote Similarity	NPD4139	Approved
0.6552	Remote Similarity	NPD4692	Approved
0.6535	Remote Similarity	NPD5697	Approved
0.6535	Remote Similarity	NPD5701	Approved
0.6517	Remote Similarity	NPD3668	Phase 3
0.6517	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6458	Remote Similarity	NPD7614	Phase 1
0.6444	Remote Similarity	NPD5329	Approved
0.6436	Remote Similarity	NPD6920	Discontinued
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD4700	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.6421	Remote Similarity	NPD7748	Approved
0.6413	Remote Similarity	NPD6903	Approved
0.6408	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD6012	Approved
0.6408	Remote Similarity	NPD6014	Approved
0.6408	Remote Similarity	NPD6372	Approved
0.6408	Remote Similarity	NPD6013	Approved
0.6395	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6098	Approved
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6364	Remote Similarity	NPD5223	Approved
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6344	Remote Similarity	NPD6904	Approved
0.6344	Remote Similarity	NPD6080	Approved
0.6344	Remote Similarity	NPD6673	Approved
0.6344	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7638	Approved
0.63	Remote Similarity	NPD5225	Approved
0.63	Remote Similarity	NPD5226	Approved
0.63	Remote Similarity	NPD5224	Approved
0.63	Remote Similarity	NPD4633	Approved
0.63	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD6705	Phase 1
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6263	Remote Similarity	NPD7639	Approved
0.6263	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7525	Registered
0.625	Remote Similarity	NPD6928	Phase 2
0.6238	Remote Similarity	NPD5175	Approved
0.6238	Remote Similarity	NPD4754	Approved
0.6238	Remote Similarity	NPD5174	Approved
0.6237	Remote Similarity	NPD5208	Approved
0.6226	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.6224	Remote Similarity	NPD7902	Approved
0.6211	Remote Similarity	NPD5693	Phase 1
0.6207	Remote Similarity	NPD4802	Phase 2
0.6207	Remote Similarity	NPD4238	Approved
0.6196	Remote Similarity	NPD5690	Phase 2
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD4632	Approved
0.6168	Remote Similarity	NPD8298	Phase 2
0.6139	Remote Similarity	NPD7632	Discontinued
0.6122	Remote Similarity	NPD7732	Phase 3
0.6117	Remote Similarity	NPD4768	Approved
0.6117	Remote Similarity	NPD4767	Approved
0.6105	Remote Similarity	NPD5692	Phase 3
0.6087	Remote Similarity	NPD634	Phase 3
0.6067	Remote Similarity	NPD5368	Approved
0.6067	Remote Similarity	NPD4695	Discontinued
0.6055	Remote Similarity	NPD6274	Approved
0.6055	Remote Similarity	NPD6868	Approved
0.6049	Remote Similarity	NPD375	Phase 2
0.6047	Remote Similarity	NPD7339	Approved
0.6047	Remote Similarity	NPD6942	Approved
0.6042	Remote Similarity	NPD5694	Approved
0.6042	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD5168	Approved
0.598	Remote Similarity	NPD5091	Approved
0.5977	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6008	Approved
0.5955	Remote Similarity	NPD4195	Approved
0.5952	Remote Similarity	NPD4747	Approved
0.5946	Remote Similarity	NPD6313	Approved
0.5946	Remote Similarity	NPD6335	Approved
0.5946	Remote Similarity	NPD6314	Approved
0.5938	Remote Similarity	NPD5207	Approved
0.5934	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6435	Approved
0.5918	Remote Similarity	NPD7900	Approved
0.5918	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6001	Approved
0.5915	Remote Similarity	NPD2266	Phase 2
0.5909	Remote Similarity	NPD6940	Discontinued
0.5905	Remote Similarity	NPD6412	Phase 2
0.5893	Remote Similarity	NPD7101	Approved
0.5893	Remote Similarity	NPD7100	Approved
0.5888	Remote Similarity	NPD5250	Approved
0.5888	Remote Similarity	NPD5249	Phase 3
0.5888	Remote Similarity	NPD4634	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