NPASS Compound

Structure

NPC215643 OpenBabel07101718192D 49 52 0 0 1 0 0 0 0 0999 V2000 7.7560 -2.6163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6628 0.1576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8825 -3.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6763 -0.0062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0241 -2.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0412 0.7662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1507 -3.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0547 0.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2922 -2.5645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4196 1.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4188 -3.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5604 -2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4331 1.2110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7980 1.9834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8285 -2.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 1.8196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1764 2.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5278 3.5283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5143 3.6921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 39 1 0 0 0 0 6 39 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 30 2 0 0 0 0 25 34 1 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 27 31 1 0 0 0 0 27 41 1 0 0 0 0 28 32 1 0 0 0 0 28 40 1 0 0 0 0 29 32 1 0 0 0 0 29 48 1 0 0 0 0 30 38 1 0 0 0 0 31 42 1 6 0 0 0 33 37 1 0 0 0 0 33 42 1 6 0 0 0 34 40 1 1 0 0 0 34 42 1 0 0 0 0 35 43 2 0 0 0 0 35 48 1 0 0 0 0 36 44 2 0 0 0 0 36 49 1 0 0 0 0 37 39 1 0 0 0 0 37 41 1 6 0 0 0 38 40 1 0 0 0 0 38 45 2 0 0 0 0 39 41 1 0 0 0 0 40 46 1 1 0 0 0 41 49 1 6 0 0 0 42 47 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	684.5
Volume:	749.111
LogP:	10.099
LogD:	5.344
LogS:	-5.683
# Rotatable Bonds:	23
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	4.9
Fsp3:	0.833
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.933
MDCK Permeability:	1.243586575583322e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.699
Plasma Protein Binding (PPB):	95.89517974853516%
Volume Distribution (VD):	1.439
Pgp-substrate:	2.192117929458618%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.4
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.261
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	5.404
Half-life (T1/2):	0.017

ADMET: Toxicity

hERG Blockers:	0.857
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.573
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.591
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.933
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC215643

Natural Product ID:	NPC215643
*Common Name:**	HDMGBAIPRPMHLP-WUHTUYPVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HDMGBAIPRPMHLP-WUHTUYPVSA-N
Standard InCHI:	InChI=1S/C42H68O7/c1-7-9-11-13-15-16-18-20-22-24-36(44)49-41-27-31(4)42(47)33(37(41)39(41,5)6)26-32(28-40(46)34(42)25-30(3)38(40)45)29-48-35(43)23-21-19-17-14-12-10-8-2/h25-26,31,33-34,37,46-47H,7-24,27-29H2,1-6H3/t31-,33+,34-,37-,40-,41+,42-/m1/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3([C@H]([C@@H]1C2(C)C)C=C(COC(=O)CCCCCCCCC)C[C@]1([C@H]3C=C(C1=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453004
PubChem CID:	24813261
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO422	Euphorbia cornigera	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	1
Others	14

Activity Type	# Activity
Cell Line	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	78.76	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	46.67	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	27.87	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	11.24	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	52.23	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	70.13	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	0.0	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	1.0	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	2.0	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	58.76	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	76.0	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	25.87	%	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Ratio	=	0.47	n.a.	PMID[495150]
NPT91	Cell Line	KB	Homo sapiens	Ratio	=	0.51	n.a.	PMID[495150]

☑ 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 NPC215643 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	228
0.1-0.2	1422
0.2-0.3	4471
0.3-0.4	7967
0.4-0.5	13862
0.5-0.6	7632
0.6-0.7	5713
0.7-0.8	1257
0.8-0.85	36
0.85-0.9	38
0.9-0.95	42
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265499
1.0	High Similarity	NPC101825
1.0	High Similarity	NPC170212
1.0	High Similarity	NPC89227
1.0	High Similarity	NPC17138
1.0	High Similarity	NPC151216
1.0	High Similarity	NPC221511
0.9904	High Similarity	NPC474937
0.9903	High Similarity	NPC96739
0.9903	High Similarity	NPC174471
0.9903	High Similarity	NPC260786
0.9903	High Similarity	NPC474871
0.9808	High Similarity	NPC475391
0.9714	High Similarity	NPC71889
0.9623	High Similarity	NPC474872
0.9537	High Similarity	NPC472760
0.9524	High Similarity	NPC158523
0.9524	High Similarity	NPC475937
0.945	High Similarity	NPC180640
0.9429	High Similarity	NPC153036
0.9364	High Similarity	NPC19336
0.9364	High Similarity	NPC185876
0.9279	High Similarity	NPC52839
0.9266	High Similarity	NPC153651
0.9196	High Similarity	NPC162009
0.9196	High Similarity	NPC257017
0.9189	High Similarity	NPC157252
0.9189	High Similarity	NPC145182
0.9189	High Similarity	NPC471128
0.9189	High Similarity	NPC471126
0.9167	High Similarity	NPC477091
0.9099	High Similarity	NPC275696
0.9099	High Similarity	NPC255081
0.9099	High Similarity	NPC5989
0.9099	High Similarity	NPC22628
0.9099	High Similarity	NPC5991
0.9099	High Similarity	NPC471108
0.9091	High Similarity	NPC10721
0.9035	High Similarity	NPC145238
0.9009	High Similarity	NPC472758
0.9009	High Similarity	NPC171905
0.9009	High Similarity	NPC471125
0.9009	High Similarity	NPC472397
0.9009	High Similarity	NPC146280
0.9009	High Similarity	NPC124676
0.9	High Similarity	NPC234858
0.9	High Similarity	NPC154363
0.9	High Similarity	NPC471127
0.8947	High Similarity	NPC472399
0.8919	High Similarity	NPC156252
0.886	High Similarity	NPC19464
0.885	High Similarity	NPC329080
0.885	High Similarity	NPC472759
0.8818	High Similarity	NPC472757
0.8793	High Similarity	NPC222307
0.8772	High Similarity	NPC472401
0.8761	High Similarity	NPC156745
0.8761	High Similarity	NPC236918
0.8739	High Similarity	NPC472400
0.8684	High Similarity	NPC475885
0.8644	High Similarity	NPC270109
0.8644	High Similarity	NPC236999
0.8462	Intermediate Similarity	NPC473802
0.8455	Intermediate Similarity	NPC163004
0.839	Intermediate Similarity	NPC473709
0.839	Intermediate Similarity	NPC473919
0.8319	Intermediate Similarity	NPC471939
0.8276	Intermediate Similarity	NPC472667
0.825	Intermediate Similarity	NPC471940
0.8241	Intermediate Similarity	NPC162973
0.8073	Intermediate Similarity	NPC476081
0.807	Intermediate Similarity	NPC71348
0.8056	Intermediate Similarity	NPC471413
0.8053	Intermediate Similarity	NPC477103
0.8051	Intermediate Similarity	NPC143755
0.8036	Intermediate Similarity	NPC322903
0.8036	Intermediate Similarity	NPC476479
0.8017	Intermediate Similarity	NPC15095
0.8017	Intermediate Similarity	NPC270958
0.8017	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC202889
0.8	Intermediate Similarity	NPC159333
0.7984	Intermediate Similarity	NPC34963
0.7984	Intermediate Similarity	NPC475139
0.7984	Intermediate Similarity	NPC180902
0.7983	Intermediate Similarity	NPC310511
0.7982	Intermediate Similarity	NPC471412
0.7967	Intermediate Similarity	NPC35109
0.7965	Intermediate Similarity	NPC273433
0.7965	Intermediate Similarity	NPC477102
0.7949	Intermediate Similarity	NPC239273
0.7944	Intermediate Similarity	NPC29952
0.7928	Intermediate Similarity	NPC118911
0.792	Intermediate Similarity	NPC476111
0.792	Intermediate Similarity	NPC469673
0.792	Intermediate Similarity	NPC58029
0.792	Intermediate Similarity	NPC469674
0.7913	Intermediate Similarity	NPC475524
0.7913	Intermediate Similarity	NPC470063
0.7913	Intermediate Similarity	NPC100267
0.7903	Intermediate Similarity	NPC279478
0.7903	Intermediate Similarity	NPC196921
0.7903	Intermediate Similarity	NPC220757
0.7903	Intermediate Similarity	NPC241935
0.7895	Intermediate Similarity	NPC5103
0.7895	Intermediate Similarity	NPC257240
0.7895	Intermediate Similarity	NPC475134
0.7895	Intermediate Similarity	NPC475563
0.789	Intermediate Similarity	NPC47024
0.789	Intermediate Similarity	NPC474718
0.789	Intermediate Similarity	NPC470074
0.7881	Intermediate Similarity	NPC257457
0.7881	Intermediate Similarity	NPC311554
0.7881	Intermediate Similarity	NPC118638
0.7881	Intermediate Similarity	NPC475372
0.7876	Intermediate Similarity	NPC189075
0.7876	Intermediate Similarity	NPC275539
0.7874	Intermediate Similarity	NPC243902
0.7863	Intermediate Similarity	NPC470793
0.7863	Intermediate Similarity	NPC270478
0.7863	Intermediate Similarity	NPC176840
0.7857	Intermediate Similarity	NPC475154
0.7857	Intermediate Similarity	NPC100017
0.7857	Intermediate Similarity	NPC471136
0.7857	Intermediate Similarity	NPC476823
0.7857	Intermediate Similarity	NPC473548
0.7857	Intermediate Similarity	NPC472645
0.7857	Intermediate Similarity	NPC182266
0.7857	Intermediate Similarity	NPC471137
0.7857	Intermediate Similarity	NPC475500
0.7857	Intermediate Similarity	NPC223356
0.7845	Intermediate Similarity	NPC477126
0.7845	Intermediate Similarity	NPC469454
0.7845	Intermediate Similarity	NPC469496
0.7845	Intermediate Similarity	NPC469463
0.7845	Intermediate Similarity	NPC25909
0.7838	Intermediate Similarity	NPC120321
0.7826	Intermediate Similarity	NPC304180
0.7826	Intermediate Similarity	NPC179798
0.7826	Intermediate Similarity	NPC475480
0.7826	Intermediate Similarity	NPC214797
0.7826	Intermediate Similarity	NPC231589
0.7826	Intermediate Similarity	NPC118860
0.7826	Intermediate Similarity	NPC475668
0.7826	Intermediate Similarity	NPC473921
0.7826	Intermediate Similarity	NPC317107
0.7823	Intermediate Similarity	NPC162495
0.7823	Intermediate Similarity	NPC221414
0.7815	Intermediate Similarity	NPC472933
0.7815	Intermediate Similarity	NPC312536
0.7807	Intermediate Similarity	NPC258543
0.7807	Intermediate Similarity	NPC241927
0.7807	Intermediate Similarity	NPC471934
0.7805	Intermediate Similarity	NPC168849
0.7805	Intermediate Similarity	NPC475273
0.7798	Intermediate Similarity	NPC216478
0.7798	Intermediate Similarity	NPC222011
0.7798	Intermediate Similarity	NPC72647
0.7798	Intermediate Similarity	NPC107806
0.7797	Intermediate Similarity	NPC475323
0.7797	Intermediate Similarity	NPC473656
0.7788	Intermediate Similarity	NPC475294
0.7788	Intermediate Similarity	NPC67321
0.7788	Intermediate Similarity	NPC187435
0.7788	Intermediate Similarity	NPC110496
0.7778	Intermediate Similarity	NPC238667
0.7778	Intermediate Similarity	NPC123117
0.7778	Intermediate Similarity	NPC138303
0.7778	Intermediate Similarity	NPC67290
0.7778	Intermediate Similarity	NPC133677
0.7778	Intermediate Similarity	NPC473964
0.7769	Intermediate Similarity	NPC222688
0.7768	Intermediate Similarity	NPC475585
0.7768	Intermediate Similarity	NPC474550
0.7768	Intermediate Similarity	NPC473577
0.7759	Intermediate Similarity	NPC4573
0.7759	Intermediate Similarity	NPC317687
0.7759	Intermediate Similarity	NPC269530
0.7759	Intermediate Similarity	NPC152117
0.7759	Intermediate Similarity	NPC277769
0.7759	Intermediate Similarity	NPC471933
0.7759	Intermediate Similarity	NPC76550
0.7759	Intermediate Similarity	NPC234042
0.7759	Intermediate Similarity	NPC170487
0.7759	Intermediate Similarity	NPC221144
0.7759	Intermediate Similarity	NPC123855
0.775	Intermediate Similarity	NPC4548
0.775	Intermediate Similarity	NPC17938
0.7748	Intermediate Similarity	NPC22388
0.7748	Intermediate Similarity	NPC475320
0.7748	Intermediate Similarity	NPC109195
0.7748	Intermediate Similarity	NPC474709
0.7748	Intermediate Similarity	NPC475038
0.7739	Intermediate Similarity	NPC253906
0.7734	Intermediate Similarity	NPC68282
0.7731	Intermediate Similarity	NPC153440
0.7731	Intermediate Similarity	NPC470420
0.7727	Intermediate Similarity	NPC469551
0.7727	Intermediate Similarity	NPC476303
0.7724	Intermediate Similarity	NPC473635

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 NPC215643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1835
0.2-0.3	3670
0.3-0.4	2209
0.4-0.5	836
0.5-0.6	226
0.6-0.7	168
0.7-0.8	11
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
0.7895	Intermediate Similarity	NPD6371	Approved
0.7565	Intermediate Similarity	NPD6881	Approved
0.7565	Intermediate Similarity	NPD6899	Approved
0.7544	Intermediate Similarity	NPD7128	Approved
0.7544	Intermediate Similarity	NPD5739	Approved
0.7544	Intermediate Similarity	NPD6402	Approved
0.7544	Intermediate Similarity	NPD6675	Approved
0.7521	Intermediate Similarity	NPD8130	Phase 1
0.7521	Intermediate Similarity	NPD6649	Approved
0.7521	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.7478	Intermediate Similarity	NPD5697	Approved
0.7478	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD8297	Approved
0.7436	Intermediate Similarity	NPD7102	Approved
0.7436	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD6883	Approved
0.7414	Intermediate Similarity	NPD7320	Approved
0.7411	Intermediate Similarity	NPD7640	Approved
0.7411	Intermediate Similarity	NPD7639	Approved
0.7391	Intermediate Similarity	NPD6008	Approved
0.7373	Intermediate Similarity	NPD6869	Approved
0.7373	Intermediate Similarity	NPD6617	Approved
0.7373	Intermediate Similarity	NPD6847	Approved
0.7355	Intermediate Similarity	NPD7115	Discovery
0.735	Intermediate Similarity	NPD6012	Approved
0.735	Intermediate Similarity	NPD6014	Approved
0.735	Intermediate Similarity	NPD6013	Approved
0.7328	Intermediate Similarity	NPD5701	Approved
0.7311	Intermediate Similarity	NPD6882	Approved
0.7288	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7604	Phase 2
0.7265	Intermediate Similarity	NPD6011	Approved
0.725	Intermediate Similarity	NPD4632	Approved
0.7232	Intermediate Similarity	NPD6084	Phase 2
0.7232	Intermediate Similarity	NPD6083	Phase 2
0.7207	Intermediate Similarity	NPD5695	Phase 3
0.7203	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6319	Approved
0.7168	Intermediate Similarity	NPD5696	Approved
0.7167	Intermediate Similarity	NPD6053	Discontinued
0.713	Intermediate Similarity	NPD5211	Phase 2
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5286	Approved
0.7105	Intermediate Similarity	NPD4696	Approved
0.7105	Intermediate Similarity	NPD5285	Approved
0.7087	Intermediate Similarity	NPD7492	Approved
0.7083	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4755	Approved
0.708	Intermediate Similarity	NPD7902	Approved
0.7073	Intermediate Similarity	NPD6009	Approved
0.7064	Intermediate Similarity	NPD1695	Approved
0.7054	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7736	Approved
0.7054	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5344	Discontinued
0.704	Intermediate Similarity	NPD6054	Approved
0.7034	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7507	Approved
0.7031	Intermediate Similarity	NPD6616	Approved
0.7027	Intermediate Similarity	NPD6399	Phase 3
0.7018	Intermediate Similarity	NPD4225	Approved
0.7009	Intermediate Similarity	NPD5141	Approved
0.6992	Remote Similarity	NPD6274	Approved
0.6984	Remote Similarity	NPD5983	Phase 2
0.6983	Remote Similarity	NPD5225	Approved
0.6983	Remote Similarity	NPD5224	Approved
0.6983	Remote Similarity	NPD5226	Approved
0.6983	Remote Similarity	NPD4633	Approved
0.6977	Remote Similarity	NPD7078	Approved
0.6977	Remote Similarity	NPD8293	Discontinued
0.6975	Remote Similarity	NPD6686	Approved
0.6964	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD5282	Discontinued
0.696	Remote Similarity	NPD7101	Approved
0.696	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD4700	Approved
0.6957	Remote Similarity	NPD6648	Approved
0.6937	Remote Similarity	NPD5693	Phase 1
0.6929	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6905	Remote Similarity	NPD6059	Approved
0.6899	Remote Similarity	NPD6336	Discontinued
0.6897	Remote Similarity	NPD5223	Approved
0.6887	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6335	Approved
0.687	Remote Similarity	NPD7319	Approved
0.686	Remote Similarity	NPD4634	Approved
0.6852	Remote Similarity	NPD1696	Phase 3
0.6852	Remote Similarity	NPD1694	Approved
0.685	Remote Similarity	NPD6016	Approved
0.685	Remote Similarity	NPD6015	Approved
0.6847	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6698	Approved
0.6838	Remote Similarity	NPD7632	Discontinued
0.6818	Remote Similarity	NPD5737	Approved
0.6818	Remote Similarity	NPD6672	Approved
0.6814	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7900	Approved
0.68	Remote Similarity	NPD6317	Approved
0.6797	Remote Similarity	NPD5988	Approved
0.6757	Remote Similarity	NPD6673	Approved
0.6757	Remote Similarity	NPD6904	Approved
0.6757	Remote Similarity	NPD6080	Approved
0.6757	Remote Similarity	NPD4753	Phase 2
0.6754	Remote Similarity	NPD5210	Approved
0.6754	Remote Similarity	NPD4629	Approved
0.6746	Remote Similarity	NPD7328	Approved
0.6746	Remote Similarity	NPD7327	Approved
0.6746	Remote Similarity	NPD6314	Approved
0.6746	Remote Similarity	NPD6313	Approved
0.6744	Remote Similarity	NPD8328	Phase 3
0.6719	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6909	Approved
0.6719	Remote Similarity	NPD8033	Approved
0.6719	Remote Similarity	NPD6908	Approved
0.6696	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD5222	Approved
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6694	Remote Similarity	NPD5128	Approved
0.6693	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6642	Remote Similarity	NPD7260	Phase 2
0.6641	Remote Similarity	NPD8377	Approved
0.6641	Remote Similarity	NPD8294	Approved
0.6639	Remote Similarity	NPD4754	Approved
0.6638	Remote Similarity	NPD5173	Approved
0.6637	Remote Similarity	NPD7515	Phase 2
0.6637	Remote Similarity	NPD6079	Approved
0.6637	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD6050	Approved
0.6637	Remote Similarity	NPD8034	Phase 2
0.6637	Remote Similarity	NPD8035	Phase 2
0.6637	Remote Similarity	NPD5281	Approved
0.6607	Remote Similarity	NPD5328	Approved
0.6589	Remote Similarity	NPD8380	Approved
0.6589	Remote Similarity	NPD8296	Approved
0.6589	Remote Similarity	NPD8335	Approved
0.6589	Remote Similarity	NPD8379	Approved
0.6589	Remote Similarity	NPD8378	Approved
0.6587	Remote Similarity	NPD6868	Approved
0.6585	Remote Similarity	NPD5248	Approved
0.6585	Remote Similarity	NPD5247	Approved
0.6585	Remote Similarity	NPD5249	Phase 3
0.6585	Remote Similarity	NPD5250	Approved
0.6585	Remote Similarity	NPD5251	Approved
0.6579	Remote Similarity	NPD4202	Approved
0.6577	Remote Similarity	NPD3573	Approved
0.656	Remote Similarity	NPD8133	Approved
0.6549	Remote Similarity	NPD5692	Phase 3
0.6549	Remote Similarity	NPD7838	Discovery
0.6545	Remote Similarity	NPD5329	Approved
0.6532	Remote Similarity	NPD5216	Approved
0.6532	Remote Similarity	NPD5215	Approved
0.6532	Remote Similarity	NPD5217	Approved
0.6491	Remote Similarity	NPD5694	Approved
0.6486	Remote Similarity	NPD5690	Phase 2
0.6486	Remote Similarity	NPD7146	Approved
0.6486	Remote Similarity	NPD7334	Approved
0.6486	Remote Similarity	NPD7521	Approved
0.6486	Remote Similarity	NPD5330	Approved
0.6486	Remote Similarity	NPD6684	Approved
0.6486	Remote Similarity	NPD6409	Approved
0.6486	Remote Similarity	NPD6098	Approved
0.6486	Remote Similarity	NPD3618	Phase 1
0.6475	Remote Similarity	NPD6412	Phase 2
0.6462	Remote Similarity	NPD7503	Approved
0.6462	Remote Similarity	NPD6921	Approved
0.6455	Remote Similarity	NPD4197	Approved
0.6452	Remote Similarity	NPD5135	Approved
0.6452	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5169	Approved
0.6435	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD5778	Approved
0.6418	Remote Similarity	NPD6033	Approved
0.6406	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5127	Approved
0.64	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4695	Discontinued
0.6372	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6903	Approved
0.6371	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5959	Approved
0.635	Remote Similarity	NPD6845	Suspended
0.6339	Remote Similarity	NPD4694	Approved
0.6339	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5280	Approved
0.6336	Remote Similarity	NPD8515	Approved
0.6336	Remote Similarity	NPD8516	Approved
0.6336	Remote Similarity	NPD8517	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