NPASS Compound

Structure

NPC102292 OpenBabel07101718322D 22 25 0 0 1 0 0 0 0 0999 V2000 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 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 -0.6634 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1420 1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 6 1 6 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 1 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 19 4 1 1 0 0 0 20 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	332.558
LogP:	3.883
LogD:	3.912
LogS:	-4.789
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.683
Synthetic Accessibility Score:	5.598
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.832
MDCK Permeability:	1.912840161821805e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	91.38813018798828%
Volume Distribution (VD):	0.983
Pgp-substrate:	5.924463748931885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.329
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.63
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	5.232
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.856
Carcinogencity:	0.111
Eye Corrosion:	0.177
Eye Irritation:	0.412
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC102292

Natural Product ID:	NPC102292
*Common Name:**	COTLKOPMPRAKRJ-NGZXWKFYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	COTLKOPMPRAKRJ-NGZXWKFYSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12-13-6-7-15-19(4)10-5-9-18(2,3)14(19)8-11-20(15,16(12)21)17(13)22/h13-15,17,22H,1,5-11H2,2-4H3/t13-,14-,15+,17-,19-,20-/m1/s1
SMILES:	C=C1[C@H]2CC[C@@H]3[C@](C1=O)([C@@H]2O)CC[C@H]1[C@@]3(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337574
PubChem CID:	10614344
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
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510600]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18161942]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19899773]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22197145]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	whole plants	Vietnam	2009-Aug	PMID[23347584]
NPO22879	Croton tonkinensis	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	3.64	%	PMID[482682]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	33.63	%	PMID[482682]

☑ 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 NPC102292 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	182
0.1-0.2	1597
0.2-0.3	6687
0.3-0.4	14975
0.4-0.5	6839
0.5-0.6	6199
0.6-0.7	4350
0.7-0.8	1618
0.8-0.85	156
0.85-0.9	46
0.9-0.95	43
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC165895
0.962	High Similarity	NPC110780
0.95	High Similarity	NPC471036
0.95	High Similarity	NPC291320
0.9405	High Similarity	NPC261994
0.9405	High Similarity	NPC149761
0.9405	High Similarity	NPC470378
0.9405	High Similarity	NPC180849
0.9294	High Similarity	NPC299185
0.9294	High Similarity	NPC278106
0.9294	High Similarity	NPC476168
0.9268	High Similarity	NPC471034
0.9268	High Similarity	NPC190704
0.9259	High Similarity	NPC118800
0.9186	High Similarity	NPC144739
0.9186	High Similarity	NPC82138
0.9186	High Similarity	NPC181594
0.9186	High Similarity	NPC59350
0.9186	High Similarity	NPC59170
0.9176	High Similarity	NPC80401
0.9146	High Similarity	NPC146683
0.908	High Similarity	NPC261333
0.908	High Similarity	NPC91772
0.908	High Similarity	NPC29247
0.908	High Similarity	NPC289539
0.908	High Similarity	NPC129004
0.908	High Similarity	NPC64006
0.908	High Similarity	NPC215271
0.908	High Similarity	NPC153775
0.908	High Similarity	NPC104371
0.908	High Similarity	NPC302008
0.908	High Similarity	NPC111524
0.908	High Similarity	NPC292374
0.908	High Similarity	NPC191094
0.908	High Similarity	NPC101233
0.9048	High Similarity	NPC259009
0.9048	High Similarity	NPC174619
0.8987	High Similarity	NPC106078
0.8977	High Similarity	NPC29112
0.8977	High Similarity	NPC231060
0.8977	High Similarity	NPC84018
0.8977	High Similarity	NPC210214
0.8977	High Similarity	NPC138245
0.8902	High Similarity	NPC46881
0.8876	High Similarity	NPC135548
0.8876	High Similarity	NPC264979
0.8876	High Similarity	NPC140242
0.8876	High Similarity	NPC13949
0.8851	High Similarity	NPC250753
0.8824	High Similarity	NPC153604
0.881	High Similarity	NPC76518
0.8721	High Similarity	NPC472739
0.869	High Similarity	NPC475745
0.869	High Similarity	NPC474482
0.8681	High Similarity	NPC16911
0.8681	High Similarity	NPC78427
0.8636	High Similarity	NPC211403
0.8636	High Similarity	NPC198242
0.8605	High Similarity	NPC472497
0.8605	High Similarity	NPC472495
0.8605	High Similarity	NPC57469
0.8587	High Similarity	NPC156324
0.8587	High Similarity	NPC127408
0.8587	High Similarity	NPC287676
0.8587	High Similarity	NPC55503
0.8587	High Similarity	NPC291785
0.8571	High Similarity	NPC475726
0.8571	High Similarity	NPC472498
0.8571	High Similarity	NPC472743
0.8506	High Similarity	NPC471724
0.8506	High Similarity	NPC474677
0.8495	Intermediate Similarity	NPC60947
0.8495	Intermediate Similarity	NPC52899
0.8495	Intermediate Similarity	NPC289148
0.8495	Intermediate Similarity	NPC471790
0.8495	Intermediate Similarity	NPC163963
0.8488	Intermediate Similarity	NPC472738
0.8488	Intermediate Similarity	NPC98236
0.8488	Intermediate Similarity	NPC269396
0.8444	Intermediate Similarity	NPC470386
0.8444	Intermediate Similarity	NPC470385
0.8444	Intermediate Similarity	NPC47853
0.8409	Intermediate Similarity	NPC119416
0.8404	Intermediate Similarity	NPC148628
0.8404	Intermediate Similarity	NPC286519
0.8404	Intermediate Similarity	NPC309388
0.8404	Intermediate Similarity	NPC88203
0.8404	Intermediate Similarity	NPC214946
0.8404	Intermediate Similarity	NPC475803
0.8404	Intermediate Similarity	NPC272472
0.8404	Intermediate Similarity	NPC246736
0.8404	Intermediate Similarity	NPC304832
0.8404	Intermediate Similarity	NPC76866
0.8372	Intermediate Similarity	NPC292553
0.8353	Intermediate Similarity	NPC175410
0.8353	Intermediate Similarity	NPC245866
0.8352	Intermediate Similarity	NPC470232
0.8333	Intermediate Similarity	NPC294263
0.8333	Intermediate Similarity	NPC328264
0.8316	Intermediate Similarity	NPC470310
0.8316	Intermediate Similarity	NPC87927
0.8316	Intermediate Similarity	NPC216114
0.8315	Intermediate Similarity	NPC126993
0.8315	Intermediate Similarity	NPC100313
0.8313	Intermediate Similarity	NPC201459
0.8295	Intermediate Similarity	NPC474719
0.8295	Intermediate Similarity	NPC471900
0.8295	Intermediate Similarity	NPC328313
0.8295	Intermediate Similarity	NPC146937
0.8293	Intermediate Similarity	NPC149249
0.8293	Intermediate Similarity	NPC212661
0.8293	Intermediate Similarity	NPC471035
0.828	Intermediate Similarity	NPC109059
0.828	Intermediate Similarity	NPC288
0.828	Intermediate Similarity	NPC471038
0.8261	Intermediate Similarity	NPC104568
0.8261	Intermediate Similarity	NPC470387
0.8261	Intermediate Similarity	NPC329910
0.8256	Intermediate Similarity	NPC474233
0.8256	Intermediate Similarity	NPC264665
0.8256	Intermediate Similarity	NPC74595
0.8242	Intermediate Similarity	NPC280804
0.8242	Intermediate Similarity	NPC475118
0.8235	Intermediate Similarity	NPC145143
0.8235	Intermediate Similarity	NPC170985
0.8235	Intermediate Similarity	NPC477858
0.8229	Intermediate Similarity	NPC13149
0.8229	Intermediate Similarity	NPC98603
0.8229	Intermediate Similarity	NPC84928
0.8222	Intermediate Similarity	NPC272746
0.8214	Intermediate Similarity	NPC164999
0.8214	Intermediate Similarity	NPC472478
0.8202	Intermediate Similarity	NPC57954
0.8202	Intermediate Similarity	NPC472477
0.8202	Intermediate Similarity	NPC213832
0.8202	Intermediate Similarity	NPC472475
0.8202	Intermediate Similarity	NPC472489
0.8191	Intermediate Similarity	NPC470388
0.8182	Intermediate Similarity	NPC475740
0.8182	Intermediate Similarity	NPC4643
0.8182	Intermediate Similarity	NPC472482
0.8182	Intermediate Similarity	NPC472481
0.8182	Intermediate Similarity	NPC134197
0.8182	Intermediate Similarity	NPC472484
0.8161	Intermediate Similarity	NPC264317
0.8161	Intermediate Similarity	NPC294438
0.8161	Intermediate Similarity	NPC474218
0.8161	Intermediate Similarity	NPC201655
0.8152	Intermediate Similarity	NPC41070
0.8152	Intermediate Similarity	NPC470229
0.8152	Intermediate Similarity	NPC472485
0.8152	Intermediate Similarity	NPC98639
0.8152	Intermediate Similarity	NPC142352
0.8144	Intermediate Similarity	NPC4115
0.8144	Intermediate Similarity	NPC12823
0.814	Intermediate Similarity	NPC471037
0.8132	Intermediate Similarity	NPC12722
0.8132	Intermediate Similarity	NPC472496
0.8118	Intermediate Similarity	NPC474484
0.8118	Intermediate Similarity	NPC103754
0.8111	Intermediate Similarity	NPC46758
0.8111	Intermediate Similarity	NPC169933
0.8111	Intermediate Similarity	NPC85173
0.8105	Intermediate Similarity	NPC46848
0.8095	Intermediate Similarity	NPC472490
0.8095	Intermediate Similarity	NPC476812
0.809	Intermediate Similarity	NPC183374
0.809	Intermediate Similarity	NPC471722
0.809	Intermediate Similarity	NPC193360
0.809	Intermediate Similarity	NPC53911
0.809	Intermediate Similarity	NPC328539
0.809	Intermediate Similarity	NPC56413
0.809	Intermediate Similarity	NPC211162
0.8085	Intermediate Similarity	NPC26270
0.8072	Intermediate Similarity	NPC476811
0.8072	Intermediate Similarity	NPC472746
0.8068	Intermediate Similarity	NPC474778
0.8068	Intermediate Similarity	NPC72133
0.8068	Intermediate Similarity	NPC2783
0.8068	Intermediate Similarity	NPC472491
0.8068	Intermediate Similarity	NPC472494
0.8068	Intermediate Similarity	NPC34190
0.8068	Intermediate Similarity	NPC145879
0.8068	Intermediate Similarity	NPC474733
0.8068	Intermediate Similarity	NPC12774
0.8068	Intermediate Similarity	NPC471042
0.8068	Intermediate Similarity	NPC474732
0.8068	Intermediate Similarity	NPC31564
0.8065	Intermediate Similarity	NPC29410
0.8065	Intermediate Similarity	NPC200054
0.8061	Intermediate Similarity	NPC471461
0.8061	Intermediate Similarity	NPC67745
0.8046	Intermediate Similarity	NPC329043
0.8046	Intermediate Similarity	NPC82902
0.8046	Intermediate Similarity	NPC85774
0.8046	Intermediate Similarity	NPC321187
0.8046	Intermediate Similarity	NPC214043
0.8046	Intermediate Similarity	NPC59453
0.8046	Intermediate Similarity	NPC58841
0.8046	Intermediate Similarity	NPC221758

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 NPC102292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2050
0.2-0.3	4222
0.3-0.4	1856
0.4-0.5	428
0.5-0.6	148
0.6-0.7	170
0.7-0.8	104
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4788	Approved
0.8276	Intermediate Similarity	NPD3618	Phase 1
0.8161	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD3133	Approved
0.8046	Intermediate Similarity	NPD4786	Approved
0.8046	Intermediate Similarity	NPD3665	Phase 1
0.8046	Intermediate Similarity	NPD3666	Approved
0.8023	Intermediate Similarity	NPD3667	Approved
0.8022	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD5328	Approved
0.7935	Intermediate Similarity	NPD4202	Approved
0.7684	Intermediate Similarity	NPD4697	Phase 3
0.7684	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5221	Approved
0.7684	Intermediate Similarity	NPD5222	Approved
0.7683	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3698	Phase 2
0.7654	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8034	Phase 2
0.7634	Intermediate Similarity	NPD8035	Phase 2
0.7629	Intermediate Similarity	NPD5286	Approved
0.7629	Intermediate Similarity	NPD4696	Approved
0.7629	Intermediate Similarity	NPD5285	Approved
0.7614	Intermediate Similarity	NPD4221	Approved
0.7614	Intermediate Similarity	NPD4223	Phase 3
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7604	Intermediate Similarity	NPD5173	Approved
0.7604	Intermediate Similarity	NPD4755	Approved
0.7579	Intermediate Similarity	NPD5210	Approved
0.7579	Intermediate Similarity	NPD4629	Approved
0.7561	Intermediate Similarity	NPD4244	Approved
0.7561	Intermediate Similarity	NPD4245	Approved
0.7551	Intermediate Similarity	NPD5223	Approved
0.7475	Intermediate Similarity	NPD5226	Approved
0.7475	Intermediate Similarity	NPD5224	Approved
0.7475	Intermediate Similarity	NPD4633	Approved
0.7475	Intermediate Similarity	NPD5211	Phase 2
0.7475	Intermediate Similarity	NPD5225	Approved
0.7473	Intermediate Similarity	NPD5279	Phase 3
0.7449	Intermediate Similarity	NPD4700	Approved
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7444	Intermediate Similarity	NPD4197	Approved
0.7412	Intermediate Similarity	NPD3703	Phase 2
0.74	Intermediate Similarity	NPD5175	Approved
0.74	Intermediate Similarity	NPD5174	Approved
0.7375	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6399	Phase 3
0.7363	Intermediate Similarity	NPD5329	Approved
0.7349	Intermediate Similarity	NPD4789	Approved
0.7327	Intermediate Similarity	NPD5141	Approved
0.7326	Intermediate Similarity	NPD6117	Approved
0.7308	Intermediate Similarity	NPD4634	Approved
0.7294	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4138	Approved
0.7283	Intermediate Similarity	NPD4689	Approved
0.7283	Intermediate Similarity	NPD4690	Approved
0.7283	Intermediate Similarity	NPD4688	Approved
0.7283	Intermediate Similarity	NPD4693	Phase 3
0.7283	Intermediate Similarity	NPD5205	Approved
0.7283	Intermediate Similarity	NPD5690	Phase 2
0.7253	Intermediate Similarity	NPD3668	Phase 3
0.7241	Intermediate Similarity	NPD6116	Phase 1
0.7228	Intermediate Similarity	NPD4754	Approved
0.7191	Intermediate Similarity	NPD4695	Discontinued
0.7191	Intermediate Similarity	NPD7525	Registered
0.7184	Intermediate Similarity	NPD5697	Approved
0.7159	Intermediate Similarity	NPD3617	Approved
0.7159	Intermediate Similarity	NPD6697	Approved
0.7159	Intermediate Similarity	NPD6118	Approved
0.7159	Intermediate Similarity	NPD6115	Approved
0.7159	Intermediate Similarity	NPD6114	Approved
0.7128	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.7115	Intermediate Similarity	NPD4729	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7115	Intermediate Similarity	NPD4730	Approved
0.7115	Intermediate Similarity	NPD5128	Approved
0.7113	Intermediate Similarity	NPD7748	Approved
0.7108	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5360	Phase 3
0.7097	Intermediate Similarity	NPD4694	Approved
0.7097	Intermediate Similarity	NPD5280	Approved
0.7097	Intermediate Similarity	NPD6684	Approved
0.7097	Intermediate Similarity	NPD5330	Approved
0.7097	Intermediate Similarity	NPD6409	Approved
0.7097	Intermediate Similarity	NPD7521	Approved
0.7097	Intermediate Similarity	NPD7334	Approved
0.7097	Intermediate Similarity	NPD7146	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD4768	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD4767	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7079	Intermediate Similarity	NPD4195	Approved
0.7075	Intermediate Similarity	NPD6650	Approved
0.7075	Intermediate Similarity	NPD6649	Approved
0.7073	Intermediate Similarity	NPD4224	Phase 2
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7071	Intermediate Similarity	NPD7902	Approved
0.7064	Intermediate Similarity	NPD7115	Discovery
0.7048	Intermediate Similarity	NPD6372	Approved
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6013	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.7048	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD5701	Approved
0.7011	Intermediate Similarity	NPD7339	Approved
0.7011	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD5696	Approved
0.6981	Remote Similarity	NPD5169	Approved
0.6981	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5248	Approved
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD5250	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6981	Remote Similarity	NPD5247	Approved
0.6981	Remote Similarity	NPD5135	Approved
0.6981	Remote Similarity	NPD5251	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.6981	Remote Similarity	NPD5249	Phase 3
0.6966	Remote Similarity	NPD3671	Phase 1
0.6952	Remote Similarity	NPD5168	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6947	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6916	Remote Similarity	NPD5127	Approved
0.6916	Remote Similarity	NPD5215	Approved
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD5216	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD5217	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6907	Remote Similarity	NPD5284	Approved
0.6907	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.6869	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4758	Discontinued
0.6852	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6832	Remote Similarity	NPD4225	Approved
0.6832	Remote Similarity	NPD7638	Approved
0.6789	Remote Similarity	NPD4632	Approved
0.6771	Remote Similarity	NPD6672	Approved
0.6771	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD7900	Approved
0.6768	Remote Similarity	NPD6001	Approved
0.6768	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6762	Remote Similarity	NPD6008	Approved
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4747	Approved
0.6744	Remote Similarity	NPD4691	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6727	Remote Similarity	NPD5167	Approved
0.6726	Remote Similarity	NPD6054	Approved
0.6726	Remote Similarity	NPD6319	Approved
0.6705	Remote Similarity	NPD6926	Approved
0.6705	Remote Similarity	NPD6924	Approved
0.6703	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6635	Remote Similarity	NPD5091	Approved
0.6633	Remote Similarity	NPD4096	Approved
0.6633	Remote Similarity	NPD5785	Approved
0.6632	Remote Similarity	NPD5363	Approved
0.663	Remote Similarity	NPD4748	Discontinued
0.6629	Remote Similarity	NPD3702	Approved
0.6628	Remote Similarity	NPD4137	Phase 3
0.6609	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD5988	Approved
0.6607	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD6317	Approved
0.6598	Remote Similarity	NPD4518	Approved
0.6598	Remote Similarity	NPD5208	Approved
0.6579	Remote Similarity	NPD6059	Approved
0.6566	Remote Similarity	NPD6411	Approved
0.6562	Remote Similarity	NPD6098	Approved
0.6559	Remote Similarity	NPD5369	Approved
0.6556	Remote Similarity	NPD6933	Approved
0.6549	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD6313	Approved
0.6549	Remote Similarity	NPD6314	Approved
0.6542	Remote Similarity	NPD6412	Phase 2
0.6531	Remote Similarity	NPD6904	Approved
0.6531	Remote Similarity	NPD6673	Approved
0.6531	Remote Similarity	NPD7285	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