NPASS Compound

Structure

NPC474771 OpenBabel07101719522D 21 22 0 0 1 0 0 0 0 0999 V2000 -1.5731 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 3.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 18 2 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.13
Volume:	298.948
LogP:	3.413
LogD:	3.04
LogS:	-3.577
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	3.483
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.716
MDCK Permeability:	3.239645957364701e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.34
Plasma Protein Binding (PPB):	80.42859649658203%
Volume Distribution (VD):	0.725
Pgp-substrate:	21.22061538696289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.685
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.857
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	13.329
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.851
AMES Toxicity:	0.214
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.601
Skin Sensitization:	0.566
Carcinogencity:	0.326
Eye Corrosion:	0.008
Eye Irritation:	0.157
Respiratory Toxicity:	0.578

Download Data

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

Natural Product: NPC474771

Natural Product ID:	NPC474771
*Common Name:**	Curvularin
IUPAC Name:	13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione
Synonyms:	Curvularin
Standard InCHIKey:	VDUIGYAPSXCJFC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3
SMILES:	CC1CCCCCC(=O)C2=C(CC(=O)O1)C=C(C=C2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482052
PubChem CID:	296197
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33114	penicillium sumatrense ma-92	Species	Aspergillaceae	Eukaryota	rhizosphere of the mangrove Lumnitzera racemosa	n.a.	n.a.	PMID[24195466]

☑ 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
GI50	60
LD50	1

Activity Type	# Activity
Cell Line	60
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	48865.24	nM	PMID[531428]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	44977.99	nM	PMID[531428]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	54325.03	nM	PMID[531428]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	41591.06	nM	PMID[531428]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	96605.09	nM	PMID[531428]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	73790.42	nM	PMID[531428]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	44463.13	nM	PMID[531428]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	90157.11	nM	PMID[531428]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	67764.15	nM	PMID[531428]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	43853.07	nM	PMID[531428]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	54075.43	nM	PMID[531428]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	76559.66	nM	PMID[531428]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	57411.65	nM	PMID[531428]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	61517.69	nM	PMID[531428]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	66834.39	nM	PMID[531428]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	59156.16	nM	PMID[531428]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	98174.79	nM	PMID[531428]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	94841.85	nM	PMID[531428]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	74301.91	nM	PMID[531428]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	55590.43	nM	PMID[531428]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531428]
NPT1102	Organism	Cucumis sativus	Cucumis sativus	LD50	=	21.0	ug ml-1	PMID[531427]

☑ 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 NPC474771 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	309
0.1-0.2	1328
0.2-0.3	3323
0.3-0.4	7951
0.4-0.5	11313
0.5-0.6	4226
0.6-0.7	7269
0.7-0.8	5921
0.8-0.85	809
0.85-0.9	178
0.9-0.95	56
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65837
1.0	High Similarity	NPC149372
1.0	High Similarity	NPC474849
1.0	High Similarity	NPC178467
0.9924	High Similarity	NPC475974
0.9773	High Similarity	NPC177307
0.9773	High Similarity	NPC9121
0.9773	High Similarity	NPC472403
0.9701	High Similarity	NPC313123
0.9701	High Similarity	NPC478217
0.9699	High Similarity	NPC474655
0.9624	High Similarity	NPC191835
0.9559	High Similarity	NPC478202
0.9559	High Similarity	NPC354984
0.9556	High Similarity	NPC472035
0.9556	High Similarity	NPC478201
0.9549	High Similarity	NPC70380
0.9478	High Similarity	NPC212693
0.9478	High Similarity	NPC94248
0.9478	High Similarity	NPC478200
0.9478	High Similarity	NPC33144
0.9403	High Similarity	NPC71256
0.9348	High Similarity	NPC210966
0.9348	High Similarity	NPC126882
0.9348	High Similarity	NPC478203
0.9333	High Similarity	NPC472602
0.9308	High Similarity	NPC41263
0.9281	High Similarity	NPC257558
0.9281	High Similarity	NPC472034
0.9275	High Similarity	NPC472006
0.927	High Similarity	NPC53649
0.927	High Similarity	NPC472603
0.927	High Similarity	NPC67650
0.927	High Similarity	NPC1704
0.9265	High Similarity	NPC105456
0.9265	High Similarity	NPC139634
0.9248	High Similarity	NPC153783
0.9214	High Similarity	NPC472033
0.9197	High Similarity	NPC472601
0.9197	High Similarity	NPC472600
0.9197	High Similarity	NPC158472
0.9185	High Similarity	NPC235115
0.9167	High Similarity	NPC17840
0.9167	High Similarity	NPC247477
0.9149	High Similarity	NPC472036
0.9137	High Similarity	NPC51106
0.9137	High Similarity	NPC159721
0.913	High Similarity	NPC472604
0.913	High Similarity	NPC472605
0.913	High Similarity	NPC158634
0.913	High Similarity	NPC244923
0.9124	High Similarity	NPC32360
0.9124	High Similarity	NPC92655
0.9124	High Similarity	NPC268052
0.9118	High Similarity	NPC194579
0.9104	High Similarity	NPC48036
0.9098	High Similarity	NPC219892
0.9098	High Similarity	NPC189823
0.9085	High Similarity	NPC240622
0.9085	High Similarity	NPC471641
0.9085	High Similarity	NPC240253
0.9085	High Similarity	NPC471642
0.9078	High Similarity	NPC107625
0.9077	High Similarity	NPC201728
0.9077	High Similarity	NPC477454
0.9077	High Similarity	NPC262671
0.9071	High Similarity	NPC42540
0.9071	High Similarity	NPC151607
0.9065	High Similarity	NPC474385
0.9008	High Similarity	NPC473691
0.9007	High Similarity	NPC83272
0.9007	High Similarity	NPC312789
0.9	High Similarity	NPC472610
0.9	High Similarity	NPC471731
0.9	High Similarity	NPC469542
0.8993	High Similarity	NPC475730
0.8993	High Similarity	NPC37530
0.8986	High Similarity	NPC88269
0.8986	High Similarity	NPC52358
0.8978	High Similarity	NPC135837
0.8971	High Similarity	NPC27407
0.8971	High Similarity	NPC278375
0.8966	High Similarity	NPC213224
0.8963	High Similarity	NPC37299
0.8963	High Similarity	NPC180261
0.8963	High Similarity	NPC43627
0.8944	High Similarity	NPC473023
0.8936	High Similarity	NPC210425
0.8936	High Similarity	NPC277426
0.8936	High Similarity	NPC86373
0.8936	High Similarity	NPC280404
0.8929	High Similarity	NPC471733
0.8929	High Similarity	NPC469579
0.8921	High Similarity	NPC99441
0.8921	High Similarity	NPC155205
0.8905	High Similarity	NPC158481
0.8904	High Similarity	NPC55092
0.8904	High Similarity	NPC275837
0.8897	High Similarity	NPC175943
0.8897	High Similarity	NPC474519
0.8897	High Similarity	NPC474394
0.8897	High Similarity	NPC474097
0.8889	High Similarity	NPC476389
0.8881	High Similarity	NPC14098
0.8881	High Similarity	NPC210320
0.8873	High Similarity	NPC473692
0.8865	High Similarity	NPC471643
0.8865	High Similarity	NPC471639
0.8849	High Similarity	NPC275356
0.8849	High Similarity	NPC162939
0.8832	High Similarity	NPC182496
0.8832	High Similarity	NPC290803
0.8832	High Similarity	NPC180905
0.8832	High Similarity	NPC142027
0.8828	High Similarity	NPC60413
0.8828	High Similarity	NPC56204
0.8819	High Similarity	NPC221352
0.8819	High Similarity	NPC153417
0.8819	High Similarity	NPC215711
0.8819	High Similarity	NPC73411
0.8806	High Similarity	NPC92624
0.8794	High Similarity	NPC250755
0.8794	High Similarity	NPC471640
0.8794	High Similarity	NPC471644
0.8777	High Similarity	NPC221104
0.8768	High Similarity	NPC50455
0.8768	High Similarity	NPC475955
0.8768	High Similarity	NPC474726
0.8768	High Similarity	NPC118919
0.8768	High Similarity	NPC291454
0.8759	High Similarity	NPC6923
0.875	High Similarity	NPC471734
0.8741	High Similarity	NPC134621
0.8741	High Similarity	NPC259942
0.8741	High Similarity	NPC147757
0.8723	High Similarity	NPC307990
0.8723	High Similarity	NPC16455
0.8723	High Similarity	NPC470842
0.8723	High Similarity	NPC90411
0.8714	High Similarity	NPC247409
0.8705	High Similarity	NPC261292
0.8705	High Similarity	NPC301915
0.8699	High Similarity	NPC469619
0.8699	High Similarity	NPC469670
0.8699	High Similarity	NPC472891
0.8692	High Similarity	NPC149246
0.8681	High Similarity	NPC471735
0.8681	High Similarity	NPC237208
0.8676	High Similarity	NPC470831
0.8676	High Similarity	NPC214702
0.8671	High Similarity	NPC95123
0.8671	High Similarity	NPC66404
0.8662	High Similarity	NPC82913
0.8662	High Similarity	NPC96692
0.8657	High Similarity	NPC209959
0.8652	High Similarity	NPC165172
0.8647	High Similarity	NPC240744
0.8647	High Similarity	NPC167055
0.8639	High Similarity	NPC200773
0.8639	High Similarity	NPC240768
0.8639	High Similarity	NPC215921
0.8639	High Similarity	NPC70016
0.8633	High Similarity	NPC472599
0.863	High Similarity	NPC270160
0.863	High Similarity	NPC476684
0.863	High Similarity	NPC237440
0.863	High Similarity	NPC4423
0.863	High Similarity	NPC84142
0.863	High Similarity	NPC77325
0.8623	High Similarity	NPC282780
0.8623	High Similarity	NPC166480
0.8621	High Similarity	NPC166583
0.8621	High Similarity	NPC53362
0.8613	High Similarity	NPC478190
0.8611	High Similarity	NPC29577
0.8603	High Similarity	NPC62219
0.86	High Similarity	NPC472404
0.8593	High Similarity	NPC95537
0.8591	High Similarity	NPC79998
0.8591	High Similarity	NPC99381
0.8582	High Similarity	NPC471819
0.8582	High Similarity	NPC57380
0.8581	High Similarity	NPC478224
0.8581	High Similarity	NPC115249
0.8581	High Similarity	NPC184284
0.8581	High Similarity	NPC76041
0.8571	High Similarity	NPC245058
0.8571	High Similarity	NPC164762
0.8562	High Similarity	NPC172329
0.8562	High Similarity	NPC2569
0.8561	High Similarity	NPC91105
0.8552	High Similarity	NPC470570
0.8552	High Similarity	NPC163846
0.8552	High Similarity	NPC225173
0.8551	High Similarity	NPC470988
0.855	High Similarity	NPC146642
0.854	High Similarity	NPC198249
0.8533	High Similarity	NPC472050
0.8531	High Similarity	NPC49108
0.8531	High Similarity	NPC105648

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 NPC474771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	908
0.2-0.3	1773
0.3-0.4	2660
0.4-0.5	1979
0.5-0.6	1092
0.6-0.7	351
0.7-0.8	116
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8714	High Similarity	NPD970	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD2534	Approved
0.8483	Intermediate Similarity	NPD2533	Approved
0.8483	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD7819	Suspended
0.8239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD7390	Discontinued
0.8028	Intermediate Similarity	NPD230	Phase 1
0.8026	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1510	Phase 2
0.7986	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD943	Approved
0.7958	Intermediate Similarity	NPD1240	Approved
0.7945	Intermediate Similarity	NPD1549	Phase 2
0.7922	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7075	Discontinued
0.7867	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD6959	Discontinued
0.7847	Intermediate Similarity	NPD1607	Approved
0.7838	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5404	Approved
0.7808	Intermediate Similarity	NPD5406	Approved
0.7808	Intermediate Similarity	NPD5405	Approved
0.7808	Intermediate Similarity	NPD2796	Approved
0.7808	Intermediate Similarity	NPD5408	Approved
0.7806	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6799	Approved
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD9545	Approved
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.7727	Intermediate Similarity	NPD4380	Phase 2
0.7727	Intermediate Similarity	NPD6599	Discontinued
0.7718	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5710	Approved
0.7688	Intermediate Similarity	NPD5711	Approved
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7681	Intermediate Similarity	NPD1201	Approved
0.7658	Intermediate Similarity	NPD3749	Approved
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3817	Phase 2
0.763	Intermediate Similarity	NPD9493	Approved
0.7628	Intermediate Similarity	NPD6801	Discontinued
0.7626	Intermediate Similarity	NPD9269	Phase 2
0.7595	Intermediate Similarity	NPD7768	Phase 2
0.7595	Intermediate Similarity	NPD3882	Suspended
0.7595	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD9268	Approved
0.7589	Intermediate Similarity	NPD1470	Approved
0.758	Intermediate Similarity	NPD2801	Approved
0.7569	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1551	Phase 2
0.7566	Intermediate Similarity	NPD1511	Approved
0.7548	Intermediate Similarity	NPD3226	Approved
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2800	Approved
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD1512	Approved
0.7465	Intermediate Similarity	NPD1164	Approved
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7448	Intermediate Similarity	NPD3764	Approved
0.7424	Intermediate Similarity	NPD74	Approved
0.7424	Intermediate Similarity	NPD9266	Approved
0.7417	Intermediate Similarity	NPD1243	Approved
0.741	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7349	Intermediate Similarity	NPD7054	Approved
0.7348	Intermediate Similarity	NPD9267	Approved
0.7348	Intermediate Similarity	NPD9263	Approved
0.7348	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9264	Approved
0.7338	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7312	Intermediate Similarity	NPD5402	Approved
0.7308	Intermediate Similarity	NPD5403	Approved
0.7308	Intermediate Similarity	NPD920	Approved
0.7305	Intermediate Similarity	NPD7472	Approved
0.7278	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7262	Intermediate Similarity	NPD5953	Discontinued
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7254	Intermediate Similarity	NPD9717	Approved
0.725	Intermediate Similarity	NPD1465	Phase 2
0.7246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5494	Approved
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7219	Intermediate Similarity	NPD6559	Discontinued
0.7211	Intermediate Similarity	NPD3268	Approved
0.719	Intermediate Similarity	NPD2654	Approved
0.7179	Intermediate Similarity	NPD5401	Approved
0.7179	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD919	Approved
0.7176	Intermediate Similarity	NPD7808	Phase 3
0.7171	Intermediate Similarity	NPD2346	Discontinued
0.7162	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5736	Approved
0.7111	Intermediate Similarity	NPD4750	Phase 3
0.711	Intermediate Similarity	NPD8150	Discontinued
0.7103	Intermediate Similarity	NPD1203	Approved
0.7101	Intermediate Similarity	NPD9281	Approved
0.7099	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD940	Approved
0.7097	Intermediate Similarity	NPD6190	Approved
0.7095	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD37	Approved
0.7075	Intermediate Similarity	NPD6832	Phase 2
0.7073	Intermediate Similarity	NPD6234	Discontinued
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD447	Suspended
0.7063	Intermediate Similarity	NPD422	Phase 1
0.7059	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD4965	Approved
0.7055	Intermediate Similarity	NPD4967	Phase 2
0.7055	Intermediate Similarity	NPD4966	Approved
0.7047	Intermediate Similarity	NPD520	Approved
0.7045	Intermediate Similarity	NPD9261	Approved
0.7042	Intermediate Similarity	NPD4626	Approved
0.7039	Intermediate Similarity	NPD7033	Discontinued
0.7014	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1247	Approved
0.6988	Remote Similarity	NPD7199	Phase 2
0.698	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5691	Approved
0.6954	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD3300	Phase 2
0.6939	Remote Similarity	NPD2798	Approved
0.6932	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2932	Approved
0.6923	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD3019	Approved
0.6905	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3926	Phase 2
0.6899	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4288	Approved
0.6879	Remote Similarity	NPD2309	Approved
0.6871	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD3266	Approved
0.6871	Remote Similarity	NPD3267	Approved
0.6868	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2313	Discontinued
0.6846	Remote Similarity	NPD4908	Phase 1
0.6845	Remote Similarity	NPD8151	Discontinued
0.6842	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5124	Phase 1
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD8312	Approved
0.6824	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1019	Discontinued
0.6821	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7003	Approved
0.6815	Remote Similarity	NPD3400	Discontinued
0.6815	Remote Similarity	NPD5048	Discontinued
0.6813	Remote Similarity	NPD6273	Approved
0.6812	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1778	Approved
0.6806	Remote Similarity	NPD17	Approved
0.6803	Remote Similarity	NPD1283	Approved
0.679	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD5353	Approved
0.6784	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3751	Discontinued
0.6784	Remote Similarity	NPD7228	Approved
0.6778	Remote Similarity	NPD6535	Approved
0.6778	Remote Similarity	NPD6534	Approved
0.6776	Remote Similarity	NPD4060	Phase 1
0.6765	Remote Similarity	NPD2403	Approved
0.6757	Remote Similarity	NPD7435	Discontinued
0.6755	Remote Similarity	NPD1296	Phase 2
0.6755	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3787	Discontinued
0.6746	Remote Similarity	NPD6808	Phase 2
0.6742	Remote Similarity	NPD4287	Approved
0.6738	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4749	Approved
0.6732	Remote Similarity	NPD6355	Discontinued
0.6731	Remote Similarity	NPD6005	Phase 3
0.6731	Remote Similarity	NPD6006	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