NPASS Compound

Structure

CID62670 OpenBabel06191715402D 30 32 0 0 1 0 0 0 0 0999 V2000 4.6200 2.7618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4392 -0.1678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6725 1.5369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2675 1.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2711 1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7297 0.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5559 1.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7391 -1.2729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9223 0.4809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7297 -0.1106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0696 0.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6164 2.5810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8605 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2435 1.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3496 -0.2839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9579 3.3598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6827 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1223 0.5592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9570 0.8101 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2435 -0.5969 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 0.6184 -0.7507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3031 4.3194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9542 3.1789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9841 3.0340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8205 2.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9901 1.0949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5240 0.2515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1431 1.1854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 4 5 1 0 0 0 0 4 9 2 0 0 0 0 5 13 2 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 12 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 14 23 2 0 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 6 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 28 2 0 0 0 0 19 30 1 0 0 0 0 20 3 1 1 0 0 0 20 30 1 0 0 0 0 21 22 1 1 0 0 0 22 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.16
Volume:	415.265
LogP:	1.124
LogD:	0.163
LogS:	-2.817
# Rotatable Bonds:	6
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.362
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.723
MDCK Permeability:	1.4045069292478729e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.121
Human Intestinal Absorption (HIA):	0.706
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	65.6238784790039%
Volume Distribution (VD):	0.265
Pgp-substrate:	23.900304794311523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.255
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.178
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	1.502
Half-life (T1/2):	0.733

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.83
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.194
Skin Sensitization:	0.411
Carcinogencity:	0.638
Eye Corrosion:	0.033
Eye Irritation:	0.078
Respiratory Toxicity:	0.391

Download Data

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

Natural Product: NPC62670

Natural Product ID:	NPC62670
*Common Name:**	Pseudolaric Acid C2
IUPAC Name:	n.a.
Synonyms:	Pseudolaric Acid C2
Standard InCHIKey:	ZPSQWDVEMDWXPJ-HPHAYBORSA-N
Standard InCHI:	InChI=1S/C22H26O8/c1-13(17(24)25)5-4-9-20(3)16-8-11-21(19(28)30-20)10-6-15(18(26)27)7-12-22(16,21)29-14(2)23/h4-6,9,16H,7-8,10-12H2,1-3H3,(H,24,25)(H,26,27)/b9-4+,13-5+/t16-,20+,21+,22-/m0/s1
SMILES:	CC(=O)O[C@@]12CCC(=CC[C@@]32CC[C@H]1[C@@](C)(/C=C/C=C(/C(=O)O)C)OC3=O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373982
PubChem CID:	6475945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346966]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	leaves,?stems	USA	n.a.	PMID[16124770]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760078]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO33269	pseudolarix kaempfri	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22700	Dacrydium comosum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21090	Chrysanthemum ornatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20772	Pedalium murex	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20262	Delia paludosa	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21914	Turnera angustifolia	Species	Passifloraceae	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	4
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[486839]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[486838]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[486839]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[486839]
NPT20	Organism	Candida albicans	Candida albicans	IZ	<	1.0	mm	PMID[486840]

☑ 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 NPC62670 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	195
0.1-0.2	1052
0.2-0.3	4105
0.3-0.4	8314
0.4-0.5	14608
0.5-0.6	8111
0.6-0.7	5459
0.7-0.8	832
0.8-0.85	9
0.85-0.9	1
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC66110
0.9787	High Similarity	NPC116139
0.9785	High Similarity	NPC244411
0.957	High Similarity	NPC9812
0.9468	High Similarity	NPC47834
0.9368	High Similarity	NPC64742
0.9271	High Similarity	NPC280963
0.9175	High Similarity	NPC206079
0.89	High Similarity	NPC309190
0.844	Intermediate Similarity	NPC13710
0.8378	Intermediate Similarity	NPC470829
0.8378	Intermediate Similarity	NPC473228
0.8351	Intermediate Similarity	NPC472705
0.8235	Intermediate Similarity	NPC475099
0.8061	Intermediate Similarity	NPC77337
0.7941	Intermediate Similarity	NPC170143
0.7941	Intermediate Similarity	NPC213947
0.7941	Intermediate Similarity	NPC108475
0.7917	Intermediate Similarity	NPC476628
0.79	Intermediate Similarity	NPC476049
0.7857	Intermediate Similarity	NPC476959
0.7849	Intermediate Similarity	NPC469617
0.7822	Intermediate Similarity	NPC90453
0.7818	Intermediate Similarity	NPC123855
0.7818	Intermediate Similarity	NPC76550
0.7807	Intermediate Similarity	NPC476962
0.78	Intermediate Similarity	NPC45579
0.7767	Intermediate Similarity	NPC40812
0.7767	Intermediate Similarity	NPC477949
0.7748	Intermediate Similarity	NPC46269
0.7748	Intermediate Similarity	NPC106395
0.7745	Intermediate Similarity	NPC469873
0.7745	Intermediate Similarity	NPC272050
0.7745	Intermediate Similarity	NPC67584
0.7745	Intermediate Similarity	NPC37408
0.7714	Intermediate Similarity	NPC146822
0.7714	Intermediate Similarity	NPC171759
0.7714	Intermediate Similarity	NPC477950
0.7692	Intermediate Similarity	NPC261377
0.7692	Intermediate Similarity	NPC255592
0.7692	Intermediate Similarity	NPC308567
0.7679	Intermediate Similarity	NPC133677
0.7679	Intermediate Similarity	NPC138303
0.7679	Intermediate Similarity	NPC67290
0.7677	Intermediate Similarity	NPC472677
0.7677	Intermediate Similarity	NPC58532
0.767	Intermediate Similarity	NPC213078
0.7664	Intermediate Similarity	NPC239162
0.7664	Intermediate Similarity	NPC100487
0.7658	Intermediate Similarity	NPC138757
0.7653	Intermediate Similarity	NPC122502
0.7642	Intermediate Similarity	NPC478156
0.7642	Intermediate Similarity	NPC475091
0.7636	Intermediate Similarity	NPC477103
0.7624	Intermediate Similarity	NPC221282
0.7624	Intermediate Similarity	NPC290651
0.7619	Intermediate Similarity	NPC469872
0.7619	Intermediate Similarity	NPC475053
0.7619	Intermediate Similarity	NPC469864
0.7611	Intermediate Similarity	NPC476963
0.7607	Intermediate Similarity	NPC55602
0.76	Intermediate Similarity	NPC212598
0.7596	Intermediate Similarity	NPC161493
0.7596	Intermediate Similarity	NPC202705
0.7593	Intermediate Similarity	NPC223450
0.7593	Intermediate Similarity	NPC314244
0.7579	Intermediate Similarity	NPC47747
0.7576	Intermediate Similarity	NPC191283
0.7573	Intermediate Similarity	NPC52044
0.7573	Intermediate Similarity	NPC171395
0.757	Intermediate Similarity	NPC110989
0.7553	Intermediate Similarity	NPC222210
0.7553	Intermediate Similarity	NPC63445
0.7551	Intermediate Similarity	NPC146850
0.7551	Intermediate Similarity	NPC245434
0.7551	Intermediate Similarity	NPC287015
0.7549	Intermediate Similarity	NPC473234
0.7549	Intermediate Similarity	NPC308656
0.7549	Intermediate Similarity	NPC60386
0.7549	Intermediate Similarity	NPC473263
0.7549	Intermediate Similarity	NPC473273
0.7547	Intermediate Similarity	NPC474742
0.7547	Intermediate Similarity	NPC150923
0.7545	Intermediate Similarity	NPC477102
0.7545	Intermediate Similarity	NPC47951
0.7544	Intermediate Similarity	NPC471145
0.7544	Intermediate Similarity	NPC239273
0.7525	Intermediate Similarity	NPC37607
0.7525	Intermediate Similarity	NPC301969
0.7524	Intermediate Similarity	NPC83895
0.7524	Intermediate Similarity	NPC470188
0.7524	Intermediate Similarity	NPC221615
0.7524	Intermediate Similarity	NPC141191
0.7524	Intermediate Similarity	NPC187761
0.7523	Intermediate Similarity	NPC470192
0.7523	Intermediate Similarity	NPC476958
0.7522	Intermediate Similarity	NPC305044
0.7522	Intermediate Similarity	NPC470953
0.7522	Intermediate Similarity	NPC265290
0.75	Intermediate Similarity	NPC78677
0.75	Intermediate Similarity	NPC203659
0.75	Intermediate Similarity	NPC185553
0.75	Intermediate Similarity	NPC98038
0.75	Intermediate Similarity	NPC59994
0.75	Intermediate Similarity	NPC313921
0.75	Intermediate Similarity	NPC126156
0.7478	Intermediate Similarity	NPC288679
0.7477	Intermediate Similarity	NPC50223
0.7477	Intermediate Similarity	NPC257240
0.7477	Intermediate Similarity	NPC473596
0.7477	Intermediate Similarity	NPC238850
0.7477	Intermediate Similarity	NPC41551
0.7477	Intermediate Similarity	NPC225353
0.7476	Intermediate Similarity	NPC477131
0.7476	Intermediate Similarity	NPC127019
0.7476	Intermediate Similarity	NPC167219
0.7475	Intermediate Similarity	NPC234038
0.7458	Intermediate Similarity	NPC472768
0.7456	Intermediate Similarity	NPC148458
0.7455	Intermediate Similarity	NPC71220
0.7455	Intermediate Similarity	NPC137286
0.7455	Intermediate Similarity	NPC220155
0.7453	Intermediate Similarity	NPC290802
0.7453	Intermediate Similarity	NPC241221
0.7451	Intermediate Similarity	NPC261607
0.7451	Intermediate Similarity	NPC111114
0.7451	Intermediate Similarity	NPC300312
0.7449	Intermediate Similarity	NPC472957
0.7449	Intermediate Similarity	NPC472958
0.7449	Intermediate Similarity	NPC196487
0.7449	Intermediate Similarity	NPC14575
0.7436	Intermediate Similarity	NPC46570
0.7434	Intermediate Similarity	NPC101965
0.7434	Intermediate Similarity	NPC101400
0.7434	Intermediate Similarity	NPC312017
0.7434	Intermediate Similarity	NPC209058
0.7434	Intermediate Similarity	NPC9848
0.7431	Intermediate Similarity	NPC472935
0.7431	Intermediate Similarity	NPC243998
0.7429	Intermediate Similarity	NPC169205
0.7426	Intermediate Similarity	NPC205548
0.7426	Intermediate Similarity	NPC106040
0.7426	Intermediate Similarity	NPC115179
0.7414	Intermediate Similarity	NPC180640
0.7414	Intermediate Similarity	NPC477092
0.7414	Intermediate Similarity	NPC472667
0.7411	Intermediate Similarity	NPC304180
0.7411	Intermediate Similarity	NPC287311
0.7411	Intermediate Similarity	NPC179798
0.7407	Intermediate Similarity	NPC280566
0.7407	Intermediate Similarity	NPC72151
0.7407	Intermediate Similarity	NPC475526
0.7407	Intermediate Similarity	NPC472755
0.7407	Intermediate Similarity	NPC475945
0.7407	Intermediate Similarity	NPC183570
0.7407	Intermediate Similarity	NPC329345
0.7407	Intermediate Similarity	NPC473283
0.7407	Intermediate Similarity	NPC475871
0.7404	Intermediate Similarity	NPC213698
0.7404	Intermediate Similarity	NPC209355
0.7404	Intermediate Similarity	NPC170120
0.7404	Intermediate Similarity	NPC304886
0.74	Intermediate Similarity	NPC477959
0.74	Intermediate Similarity	NPC478145
0.74	Intermediate Similarity	NPC86005
0.7391	Intermediate Similarity	NPC475305
0.7387	Intermediate Similarity	NPC475274
0.7379	Intermediate Similarity	NPC40821
0.7379	Intermediate Similarity	NPC32862
0.7379	Intermediate Similarity	NPC272293
0.7379	Intermediate Similarity	NPC153590
0.7374	Intermediate Similarity	NPC471185
0.7373	Intermediate Similarity	NPC107493
0.7368	Intermediate Similarity	NPC476627
0.7353	Intermediate Similarity	NPC145666
0.7353	Intermediate Similarity	NPC473448
0.7353	Intermediate Similarity	NPC472866
0.735	Intermediate Similarity	NPC184555
0.735	Intermediate Similarity	NPC19336
0.735	Intermediate Similarity	NPC185876
0.735	Intermediate Similarity	NPC143755
0.735	Intermediate Similarity	NPC472004
0.7345	Intermediate Similarity	NPC475970
0.7345	Intermediate Similarity	NPC90952
0.7345	Intermediate Similarity	NPC66108
0.7339	Intermediate Similarity	NPC474741
0.7339	Intermediate Similarity	NPC169843
0.7339	Intermediate Similarity	NPC272632
0.7339	Intermediate Similarity	NPC121099
0.7333	Intermediate Similarity	NPC29952
0.7333	Intermediate Similarity	NPC142529
0.7333	Intermediate Similarity	NPC91771
0.7333	Intermediate Similarity	NPC230800
0.7333	Intermediate Similarity	NPC18019
0.7333	Intermediate Similarity	NPC24956
0.7328	Intermediate Similarity	NPC475401
0.7328	Intermediate Similarity	NPC475309
0.7328	Intermediate Similarity	NPC472760
0.7327	Intermediate Similarity	NPC153805
0.7327	Intermediate Similarity	NPC227379

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 NPC62670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1324
0.2-0.3	3658
0.3-0.4	2608
0.4-0.5	893
0.5-0.6	281
0.6-0.7	209
0.7-0.8	9
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
0.7477	Intermediate Similarity	NPD6371	Approved
0.7353	Intermediate Similarity	NPD5785	Approved
0.7238	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5779	Approved
0.7212	Intermediate Similarity	NPD5778	Approved
0.7207	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7983	Approved
0.7115	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD7839	Suspended
0.6952	Remote Similarity	NPD5284	Approved
0.6952	Remote Similarity	NPD6411	Approved
0.6952	Remote Similarity	NPD5281	Approved
0.6917	Remote Similarity	NPD6319	Approved
0.69	Remote Similarity	NPD5209	Approved
0.688	Remote Similarity	NPD7319	Approved
0.6863	Remote Similarity	NPD5363	Approved
0.6857	Remote Similarity	NPD6698	Approved
0.6857	Remote Similarity	NPD46	Approved
0.6842	Remote Similarity	NPD6686	Approved
0.6822	Remote Similarity	NPD5282	Discontinued
0.6818	Remote Similarity	NPD7639	Approved
0.6818	Remote Similarity	NPD7640	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.6796	Remote Similarity	NPD5786	Approved
0.6792	Remote Similarity	NPD5693	Phase 1
0.6792	Remote Similarity	NPD5694	Approved
0.6774	Remote Similarity	NPD7507	Approved
0.6762	Remote Similarity	NPD6101	Approved
0.6762	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD5697	Approved
0.6733	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7638	Approved
0.6698	Remote Similarity	NPD5692	Phase 3
0.6698	Remote Similarity	NPD5207	Approved
0.6698	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5362	Discontinued
0.6638	Remote Similarity	NPD6012	Approved
0.6638	Remote Similarity	NPD6013	Approved
0.6638	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6636	Remote Similarity	NPD6050	Approved
0.661	Remote Similarity	NPD6882	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6604	Remote Similarity	NPD1695	Approved
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6585	Remote Similarity	NPD7503	Approved
0.6585	Remote Similarity	NPD8517	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6581	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6577	Remote Similarity	NPD4225	Approved
0.6569	Remote Similarity	NPD4270	Approved
0.6569	Remote Similarity	NPD6435	Approved
0.6569	Remote Similarity	NPD4269	Approved
0.656	Remote Similarity	NPD7492	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6552	Remote Similarity	NPD6011	Approved
0.6549	Remote Similarity	NPD5211	Phase 2
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD8130	Phase 1
0.6525	Remote Similarity	NPD6847	Approved
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6512	Remote Similarity	NPD7260	Phase 2
0.6509	Remote Similarity	NPD4518	Approved
0.6508	Remote Similarity	NPD6616	Approved
0.6504	Remote Similarity	NPD6054	Approved
0.6496	Remote Similarity	NPD6373	Approved
0.6496	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD4249	Approved
0.6476	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5690	Phase 2
0.6476	Remote Similarity	NPD4694	Approved
0.6476	Remote Similarity	NPD5280	Approved
0.6471	Remote Similarity	NPD5369	Approved
0.6466	Remote Similarity	NPD5701	Approved
0.6457	Remote Similarity	NPD7078	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6452	Remote Similarity	NPD6015	Approved
0.6449	Remote Similarity	NPD6904	Approved
0.6449	Remote Similarity	NPD6080	Approved
0.6449	Remote Similarity	NPD6673	Approved
0.6441	Remote Similarity	NPD4634	Approved
0.6435	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD4250	Approved
0.6415	Remote Similarity	NPD3573	Approved
0.6415	Remote Similarity	NPD4251	Approved
0.641	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD4221	Approved
0.6408	Remote Similarity	NPD4223	Phase 3
0.6406	Remote Similarity	NPD7736	Approved
0.64	Remote Similarity	NPD5988	Approved
0.64	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD6009	Approved
0.6381	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD1694	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6373	Remote Similarity	NPD4821	Approved
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4252	Approved
0.6373	Remote Similarity	NPD4819	Approved
0.6373	Remote Similarity	NPD4822	Approved
0.6373	Remote Similarity	NPD5368	Approved
0.6373	Remote Similarity	NPD4820	Approved
0.6372	Remote Similarity	NPD6648	Approved
0.6372	Remote Similarity	NPD5285	Approved
0.6372	Remote Similarity	NPD5286	Approved
0.6372	Remote Similarity	NPD6404	Discontinued
0.6372	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD8039	Approved
0.6355	Remote Similarity	NPD5208	Approved
0.6346	Remote Similarity	NPD6695	Phase 3
0.6346	Remote Similarity	NPD7154	Phase 3
0.6328	Remote Similarity	NPD8074	Phase 3
0.632	Remote Similarity	NPD5983	Phase 2
0.6306	Remote Similarity	NPD5654	Approved
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD4753	Phase 2
0.6286	Remote Similarity	NPD4197	Approved
0.6286	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5226	Approved
0.6261	Remote Similarity	NPD5225	Approved
0.6261	Remote Similarity	NPD4633	Approved
0.6261	Remote Similarity	NPD5224	Approved
0.6261	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6059	Approved
0.6239	Remote Similarity	NPD4096	Approved
0.6226	Remote Similarity	NPD5329	Approved
0.6226	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7604	Phase 2
0.622	Remote Similarity	NPD7829	Approved
0.622	Remote Similarity	NPD7830	Approved
0.621	Remote Similarity	NPD7328	Approved
0.621	Remote Similarity	NPD7327	Approved
0.6207	Remote Similarity	NPD5175	Approved
0.6207	Remote Similarity	NPD5174	Approved
0.6204	Remote Similarity	NPD6672	Approved
0.6204	Remote Similarity	NPD5737	Approved
0.6202	Remote Similarity	NPD8293	Discontinued
0.6195	Remote Similarity	NPD4755	Approved
0.6195	Remote Similarity	NPD5959	Approved
0.619	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD5332	Approved
0.6186	Remote Similarity	NPD6412	Phase 2
0.6182	Remote Similarity	NPD6079	Approved
0.6179	Remote Similarity	NPD6274	Approved
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4268	Approved
0.6174	Remote Similarity	NPD5344	Discontinued
0.6174	Remote Similarity	NPD5223	Approved
0.6168	Remote Similarity	NPD4138	Approved
0.6168	Remote Similarity	NPD7334	Approved
0.6168	Remote Similarity	NPD5205	Approved
0.6168	Remote Similarity	NPD5279	Phase 3
0.6168	Remote Similarity	NPD6684	Approved
0.6168	Remote Similarity	NPD4690	Approved
0.6168	Remote Similarity	NPD4693	Phase 3
0.6168	Remote Similarity	NPD7146	Approved
0.6168	Remote Similarity	NPD6098	Approved
0.6168	Remote Similarity	NPD5330	Approved
0.6168	Remote Similarity	NPD4688	Approved
0.6168	Remote Similarity	NPD7521	Approved
0.6168	Remote Similarity	NPD4623	Approved
0.6168	Remote Similarity	NPD6409	Approved
0.6168	Remote Similarity	NPD4689	Approved
0.6168	Remote Similarity	NPD4519	Discontinued
0.6167	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7516	Approved
0.616	Remote Similarity	NPD7100	Approved
0.616	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD4790	Discontinued
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4730	Approved
0.6134	Remote Similarity	NPD4729	Approved
0.6129	Remote Similarity	NPD6317	Approved
0.6126	Remote Similarity	NPD6399	Phase 3
0.6124	Remote Similarity	NPD6336	Discontinued
0.6124	Remote Similarity	NPD8273	Phase 1
0.6117	Remote Similarity	NPD4195	Approved
0.6116	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7524	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