NPASS Compound

Structure

NPC473267 OpenBabel07101718292D 22 26 0 0 1 0 0 0 0 0999 V2000 -2.7198 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1058 -0.5692 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 -0.9269 1.6054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 -1.6054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 -1.0703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 2.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6174 -0.1322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7446 1.8714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7358 0.6064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6608 0.1060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2955 1.0369 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9269 0.5351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7806 0.5351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6720 0.2550 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 -2.7806 1.6054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 18 1 0 0 0 0 14 17 1 6 0 0 0 14 19 1 0 0 0 0 15 17 1 6 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 1 1 6 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	326.638
LogP:	3.224
LogD:	2.867
LogS:	-1.328
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	6.251
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.242
MDCK Permeability:	9.418326953891665e-06
Pgp-inhibitor:	0.308
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	81.98111724853516%
Volume Distribution (VD):	0.697
Pgp-substrate:	13.216691017150879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	19.117
Half-life (T1/2):	0.513

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.581
Skin Sensitization:	0.645
Carcinogencity:	0.907
Eye Corrosion:	0.043
Eye Irritation:	0.046
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC473267

Natural Product ID:	NPC473267
*Common Name:**	GEANNTVLCDDBTE-TXXJSFQBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GEANNTVLCDDBTE-TXXJSFQBSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-17-6-5-16(22)19(3,11-21)14(17)4-7-20-9-13-12(8-15(17)20)18(13,2)10-20/h12-15,21H,4-11H2,1-3H3/t12-,13?,14-,15-,17+,18-,19+,20-/m0/s1
SMILES:	CC12CCC(=O)C(C1CCC34C2CC5C(C3)C5(C4)C)(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388791
PubChem CID:	44423992
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
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547457]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12671	Croton zambesicus	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	40400.0	nM	PMID[515804]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	6300.0	nM	PMID[515804]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	17.0	%	PMID[515804]

☑ 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 NPC473267 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	342
0.1-0.2	3942
0.2-0.3	16578
0.3-0.4	8723
0.4-0.5	5710
0.5-0.6	5055
0.6-0.7	1881
0.7-0.8	377
0.8-0.85	65
0.85-0.9	22
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC476731
0.9041	High Similarity	NPC52951
0.9014	High Similarity	NPC273366
0.8986	High Similarity	NPC477850
0.8857	High Similarity	NPC58057
0.8857	High Similarity	NPC320549
0.8857	High Similarity	NPC156277
0.8857	High Similarity	NPC151018
0.8841	High Similarity	NPC324607
0.8841	High Similarity	NPC6120
0.8841	High Similarity	NPC321732
0.8841	High Similarity	NPC327728
0.8841	High Similarity	NPC213178
0.8841	High Similarity	NPC131892
0.8767	High Similarity	NPC264602
0.8767	High Similarity	NPC475031
0.8732	High Similarity	NPC232112
0.8732	High Similarity	NPC310766
0.8696	High Similarity	NPC474954
0.8657	High Similarity	NPC128608
0.8611	High Similarity	NPC477930
0.8611	High Similarity	NPC254340
0.8611	High Similarity	NPC472854
0.8592	High Similarity	NPC89310
0.8571	High Similarity	NPC469941
0.8571	High Similarity	NPC476734
0.8571	High Similarity	NPC474962
0.8571	High Similarity	NPC252032
0.8571	High Similarity	NPC319671
0.8551	High Similarity	NPC130459
0.8551	High Similarity	NPC474221
0.8551	High Similarity	NPC478180
0.8514	High Similarity	NPC477918
0.8493	Intermediate Similarity	NPC472311
0.8493	Intermediate Similarity	NPC195155
0.8493	Intermediate Similarity	NPC97534
0.8493	Intermediate Similarity	NPC125767
0.8493	Intermediate Similarity	NPC21220
0.8493	Intermediate Similarity	NPC174964
0.8451	Intermediate Similarity	NPC477929
0.8429	Intermediate Similarity	NPC473225
0.8378	Intermediate Similarity	NPC5767
0.8378	Intermediate Similarity	NPC472486
0.8378	Intermediate Similarity	NPC472487
0.8378	Intermediate Similarity	NPC475742
0.8378	Intermediate Similarity	NPC477933
0.8378	Intermediate Similarity	NPC477932
0.8356	Intermediate Similarity	NPC133922
0.8356	Intermediate Similarity	NPC280026
0.8356	Intermediate Similarity	NPC167702
0.8312	Intermediate Similarity	NPC469745
0.831	Intermediate Similarity	NPC64466
0.8267	Intermediate Similarity	NPC23884
0.8267	Intermediate Similarity	NPC221420
0.8243	Intermediate Similarity	NPC477934
0.8243	Intermediate Similarity	NPC212733
0.8243	Intermediate Similarity	NPC24014
0.8243	Intermediate Similarity	NPC159789
0.8243	Intermediate Similarity	NPC27349
0.8228	Intermediate Similarity	NPC319909
0.8219	Intermediate Similarity	NPC474123
0.8205	Intermediate Similarity	NPC477858
0.8194	Intermediate Similarity	NPC108131
0.8182	Intermediate Similarity	NPC477851
0.8169	Intermediate Similarity	NPC260319
0.8169	Intermediate Similarity	NPC103647
0.8169	Intermediate Similarity	NPC2568
0.8169	Intermediate Similarity	NPC180777
0.8158	Intermediate Similarity	NPC185465
0.8143	Intermediate Similarity	NPC477931
0.8143	Intermediate Similarity	NPC268736
0.8143	Intermediate Similarity	NPC42060
0.8133	Intermediate Similarity	NPC4209
0.8101	Intermediate Similarity	NPC217559
0.8101	Intermediate Similarity	NPC268578
0.8101	Intermediate Similarity	NPC292458
0.8101	Intermediate Similarity	NPC472744
0.8082	Intermediate Similarity	NPC469940
0.8077	Intermediate Similarity	NPC77311
0.8077	Intermediate Similarity	NPC12933
0.8056	Intermediate Similarity	NPC196197
0.8052	Intermediate Similarity	NPC201459
0.8052	Intermediate Similarity	NPC320144
0.8026	Intermediate Similarity	NPC298168
0.8026	Intermediate Similarity	NPC207010
0.8026	Intermediate Similarity	NPC143133
0.8026	Intermediate Similarity	NPC477919
0.8026	Intermediate Similarity	NPC474404
0.8026	Intermediate Similarity	NPC180199
0.8026	Intermediate Similarity	NPC317913
0.8026	Intermediate Similarity	NPC106078
0.8025	Intermediate Similarity	NPC302111
0.8	Intermediate Similarity	NPC179858
0.8	Intermediate Similarity	NPC474996
0.8	Intermediate Similarity	NPC471044
0.8	Intermediate Similarity	NPC50438
0.8	Intermediate Similarity	NPC473336
0.7975	Intermediate Similarity	NPC477935
0.7975	Intermediate Similarity	NPC110780
0.7975	Intermediate Similarity	NPC46881
0.7949	Intermediate Similarity	NPC470609
0.7922	Intermediate Similarity	NPC224802
0.7922	Intermediate Similarity	NPC199965
0.7922	Intermediate Similarity	NPC476732
0.7922	Intermediate Similarity	NPC80089
0.7922	Intermediate Similarity	NPC324700
0.7922	Intermediate Similarity	NPC34046
0.7922	Intermediate Similarity	NPC171426
0.791	Intermediate Similarity	NPC476735
0.7901	Intermediate Similarity	NPC201655
0.7901	Intermediate Similarity	NPC76518
0.7879	Intermediate Similarity	NPC474105
0.7875	Intermediate Similarity	NPC471036
0.7875	Intermediate Similarity	NPC15821
0.7875	Intermediate Similarity	NPC291320
0.7857	Intermediate Similarity	NPC69149
0.7848	Intermediate Similarity	NPC474484
0.7848	Intermediate Similarity	NPC103754
0.7838	Intermediate Similarity	NPC126642
0.7838	Intermediate Similarity	NPC290058
0.7838	Intermediate Similarity	NPC472309
0.7831	Intermediate Similarity	NPC146937
0.7821	Intermediate Similarity	NPC245029
0.7821	Intermediate Similarity	NPC472310
0.7821	Intermediate Similarity	NPC80891
0.7821	Intermediate Similarity	NPC31302
0.7821	Intermediate Similarity	NPC201276
0.7805	Intermediate Similarity	NPC474448
0.7805	Intermediate Similarity	NPC70661
0.7805	Intermediate Similarity	NPC472745
0.7778	Intermediate Similarity	NPC475884
0.7778	Intermediate Similarity	NPC473230
0.7763	Intermediate Similarity	NPC132064
0.775	Intermediate Similarity	NPC145143
0.775	Intermediate Similarity	NPC61107
0.775	Intermediate Similarity	NPC30583
0.775	Intermediate Similarity	NPC317066
0.775	Intermediate Similarity	NPC477936
0.775	Intermediate Similarity	NPC328007
0.775	Intermediate Similarity	NPC289486
0.7746	Intermediate Similarity	NPC473276
0.7746	Intermediate Similarity	NPC474380
0.7746	Intermediate Similarity	NPC41577
0.7738	Intermediate Similarity	NPC24705
0.7738	Intermediate Similarity	NPC56962
0.7733	Intermediate Similarity	NPC81759
0.7733	Intermediate Similarity	NPC282905
0.7733	Intermediate Similarity	NPC477229
0.7733	Intermediate Similarity	NPC68426
0.7722	Intermediate Similarity	NPC472853
0.7714	Intermediate Similarity	NPC114891
0.7711	Intermediate Similarity	NPC263802
0.7711	Intermediate Similarity	NPC57469
0.7711	Intermediate Similarity	NPC202937
0.7692	Intermediate Similarity	NPC329117
0.7692	Intermediate Similarity	NPC478128
0.7683	Intermediate Similarity	NPC102292
0.7683	Intermediate Similarity	NPC471034
0.7683	Intermediate Similarity	NPC190704
0.7654	Intermediate Similarity	NPC259173
0.7654	Intermediate Similarity	NPC475726
0.7654	Intermediate Similarity	NPC163616
0.7654	Intermediate Similarity	NPC327451
0.7654	Intermediate Similarity	NPC472743
0.7654	Intermediate Similarity	NPC175410
0.7632	Intermediate Similarity	NPC168511
0.7632	Intermediate Similarity	NPC130011
0.7632	Intermediate Similarity	NPC159325
0.7625	Intermediate Similarity	NPC58631
0.7625	Intermediate Similarity	NPC50658
0.7612	Intermediate Similarity	NPC143597
0.7612	Intermediate Similarity	NPC151464
0.7576	Intermediate Similarity	NPC288296
0.7576	Intermediate Similarity	NPC53245
0.7571	Intermediate Similarity	NPC218585
0.7571	Intermediate Similarity	NPC148174
0.7571	Intermediate Similarity	NPC71460
0.7568	Intermediate Similarity	NPC241085
0.7568	Intermediate Similarity	NPC299948
0.7568	Intermediate Similarity	NPC470830
0.7564	Intermediate Similarity	NPC169389
0.7561	Intermediate Similarity	NPC475745
0.7561	Intermediate Similarity	NPC474482
0.7561	Intermediate Similarity	NPC474233
0.7534	Intermediate Similarity	NPC472984
0.7532	Intermediate Similarity	NPC267753
0.7531	Intermediate Similarity	NPC268040
0.7531	Intermediate Similarity	NPC121121
0.7529	Intermediate Similarity	NPC61688
0.7529	Intermediate Similarity	NPC122116
0.75	Intermediate Similarity	NPC96496
0.75	Intermediate Similarity	NPC259009
0.75	Intermediate Similarity	NPC134197
0.75	Intermediate Similarity	NPC252714
0.75	Intermediate Similarity	NPC164999
0.75	Intermediate Similarity	NPC266431
0.75	Intermediate Similarity	NPC472482
0.75	Intermediate Similarity	NPC243469
0.75	Intermediate Similarity	NPC472481
0.75	Intermediate Similarity	NPC472484

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 NPC473267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	3866
0.2-0.3	3564
0.3-0.4	784
0.4-0.5	221
0.5-0.6	255
0.6-0.7	51
0.7-0.8	17
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD3171	Clinical (unspecified phase)
0.8986	High Similarity	NPD4789	Approved
0.8857	High Similarity	NPD4809	Clinical (unspecified phase)
0.8857	High Similarity	NPD4808	Clinical (unspecified phase)
0.8841	High Similarity	NPD3698	Phase 2
0.8841	High Similarity	NPD3700	Clinical (unspecified phase)
0.8841	High Similarity	NPD3699	Clinical (unspecified phase)
0.8714	High Similarity	NPD4245	Approved
0.8714	High Similarity	NPD4244	Approved
0.8429	Intermediate Similarity	NPD5360	Phase 3
0.8429	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD4224	Phase 2
0.8356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3703	Phase 2
0.8133	Intermediate Similarity	NPD6117	Approved
0.8082	Intermediate Similarity	NPD4758	Discontinued
0.8082	Intermediate Similarity	NPD6081	Approved
0.8026	Intermediate Similarity	NPD6116	Phase 1
0.7922	Intermediate Similarity	NPD3671	Phase 1
0.7922	Intermediate Similarity	NPD6115	Approved
0.7922	Intermediate Similarity	NPD6697	Approved
0.7922	Intermediate Similarity	NPD6118	Approved
0.7922	Intermediate Similarity	NPD6114	Approved
0.7763	Intermediate Similarity	NPD3702	Approved
0.7654	Intermediate Similarity	NPD4788	Approved
0.76	Intermediate Similarity	NPD5777	Approved
0.7468	Intermediate Similarity	NPD5364	Discontinued
0.7349	Intermediate Similarity	NPD4786	Approved
0.7317	Intermediate Similarity	NPD3667	Approved
0.7262	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7105	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3617	Approved
0.7013	Intermediate Similarity	NPD4787	Phase 1
0.6977	Remote Similarity	NPD3618	Phase 1
0.6932	Remote Similarity	NPD5328	Approved
0.6932	Remote Similarity	NPD4753	Phase 2
0.6905	Remote Similarity	NPD4223	Phase 3
0.6905	Remote Similarity	NPD4221	Approved
0.6786	Remote Similarity	NPD4139	Approved
0.6786	Remote Similarity	NPD4692	Approved
0.6782	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5279	Phase 3
0.6778	Remote Similarity	NPD6079	Approved
0.6744	Remote Similarity	NPD4197	Approved
0.6703	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6593	Remote Similarity	NPD8035	Phase 2
0.6593	Remote Similarity	NPD8034	Phase 2
0.6591	Remote Similarity	NPD4690	Approved
0.6591	Remote Similarity	NPD5205	Approved
0.6591	Remote Similarity	NPD4688	Approved
0.6591	Remote Similarity	NPD4693	Phase 3
0.6591	Remote Similarity	NPD4689	Approved
0.6591	Remote Similarity	NPD4138	Approved
0.6575	Remote Similarity	NPD3198	Approved
0.6559	Remote Similarity	NPD5210	Approved
0.6559	Remote Similarity	NPD4629	Approved
0.6552	Remote Similarity	NPD3668	Phase 3
0.6538	Remote Similarity	NPD6705	Phase 1
0.6522	Remote Similarity	NPD6399	Phase 3
0.6489	Remote Similarity	NPD5222	Approved
0.6489	Remote Similarity	NPD5221	Approved
0.6489	Remote Similarity	NPD4697	Phase 3
0.6489	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6084	Phase 2
0.6421	Remote Similarity	NPD5173	Approved
0.6421	Remote Similarity	NPD4755	Approved
0.6421	Remote Similarity	NPD6083	Phase 2
0.6404	Remote Similarity	NPD5690	Phase 2
0.6404	Remote Similarity	NPD4694	Approved
0.6404	Remote Similarity	NPD5280	Approved
0.6344	Remote Similarity	NPD5133	Approved
0.6338	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD8418	Phase 2
0.6289	Remote Similarity	NPD4700	Approved
0.6289	Remote Similarity	NPD5286	Approved
0.6289	Remote Similarity	NPD4696	Approved
0.6289	Remote Similarity	NPD5285	Approved
0.6279	Remote Similarity	NPD7525	Registered
0.6279	Remote Similarity	NPD6928	Phase 2
0.6265	Remote Similarity	NPD6942	Approved
0.6265	Remote Similarity	NPD7339	Approved
0.6264	Remote Similarity	NPD6672	Approved
0.6264	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5737	Approved
0.6237	Remote Similarity	NPD7515	Phase 2
0.6224	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD7521	Approved
0.6222	Remote Similarity	NPD7334	Approved
0.6222	Remote Similarity	NPD7146	Approved
0.6222	Remote Similarity	NPD6684	Approved
0.6222	Remote Similarity	NPD6409	Approved
0.6222	Remote Similarity	NPD5330	Approved
0.6211	Remote Similarity	NPD5695	Phase 3
0.62	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5696	Approved
0.6173	Remote Similarity	NPD4747	Approved
0.6163	Remote Similarity	NPD4195	Approved
0.6162	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD4633	Approved
0.6162	Remote Similarity	NPD5211	Phase 2
0.6162	Remote Similarity	NPD5225	Approved
0.6162	Remote Similarity	NPD5224	Approved
0.6139	Remote Similarity	NPD6920	Discontinued
0.6111	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4754	Approved
0.61	Remote Similarity	NPD5174	Approved
0.61	Remote Similarity	NPD5175	Approved
0.6092	Remote Similarity	NPD4695	Discontinued
0.6087	Remote Similarity	NPD6903	Approved
0.6064	Remote Similarity	NPD5281	Approved
0.6064	Remote Similarity	NPD5284	Approved
0.6058	Remote Similarity	NPD4634	Approved
0.6049	Remote Similarity	NPD4137	Phase 3
0.6047	Remote Similarity	NPD4776	Phase 2
0.6047	Remote Similarity	NPD4238	Approved
0.6047	Remote Similarity	NPD4802	Phase 2
0.6047	Remote Similarity	NPD4777	Suspended
0.6044	Remote Similarity	NPD6098	Approved
0.6044	Remote Similarity	NPD4623	Approved
0.6044	Remote Similarity	NPD4519	Discontinued
0.6042	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5141	Approved
0.6029	Remote Similarity	NPD344	Approved
0.6029	Remote Similarity	NPD345	Approved
0.6029	Remote Similarity	NPD343	Approved
0.6019	Remote Similarity	NPD6415	Discontinued
0.598	Remote Similarity	NPD7128	Approved
0.598	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD5739	Approved
0.598	Remote Similarity	NPD4768	Approved
0.598	Remote Similarity	NPD6675	Approved
0.598	Remote Similarity	NPD4767	Approved
0.5976	Remote Similarity	NPD4691	Approved
0.5957	Remote Similarity	NPD4096	Approved
0.5952	Remote Similarity	NPD6926	Approved
0.5952	Remote Similarity	NPD6924	Approved
0.5938	Remote Similarity	NPD6001	Approved
0.5938	Remote Similarity	NPD7748	Approved
0.5926	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5701	Approved
0.5922	Remote Similarity	NPD5697	Approved
0.5914	Remote Similarity	NPD5208	Approved
0.5909	Remote Similarity	NPD4748	Discontinued
0.5904	Remote Similarity	NPD4243	Approved
0.5872	Remote Similarity	NPD7115	Discovery
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD5168	Approved
0.5865	Remote Similarity	NPD5128	Approved
0.5865	Remote Similarity	NPD6011	Approved
0.5865	Remote Similarity	NPD4730	Approved
0.5865	Remote Similarity	NPD4729	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5862	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7638	Approved
0.5851	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6080	Approved
0.5851	Remote Similarity	NPD6673	Approved
0.5851	Remote Similarity	NPD6904	Approved
0.5833	Remote Similarity	NPD3186	Phase 1
0.5814	Remote Similarity	NPD6933	Approved
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD6373	Approved
0.581	Remote Similarity	NPD6013	Approved
0.581	Remote Similarity	NPD6014	Approved
0.58	Remote Similarity	NPD7639	Approved
0.58	Remote Similarity	NPD7640	Approved
0.5797	Remote Similarity	NPD385	Approved
0.5797	Remote Similarity	NPD384	Approved
0.5769	Remote Similarity	NPD6412	Phase 2
0.5765	Remote Similarity	NPD4058	Approved
0.5765	Remote Similarity	NPD4785	Approved
0.5765	Remote Similarity	NPD5733	Approved
0.5765	Remote Similarity	NPD4784	Approved
0.5765	Remote Similarity	NPD4687	Approved
0.5758	Remote Similarity	NPD7902	Approved
0.5755	Remote Similarity	NPD5250	Approved
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD5169	Approved
0.5755	Remote Similarity	NPD5249	Phase 3
0.5755	Remote Similarity	NPD5247	Approved
0.5755	Remote Similarity	NPD5135	Approved
0.5755	Remote Similarity	NPD5251	Approved
0.5755	Remote Similarity	NPD5248	Approved
0.5755	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6883	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5745	Remote Similarity	NPD4518	Approved
0.5743	Remote Similarity	NPD1700	Approved
0.5729	Remote Similarity	NPD5693	Phase 1
0.5714	Remote Similarity	NPD5276	Approved
0.5701	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD5215	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