NPASS Compound

Structure

CID191521 OpenBabel06191715572D 24 26 0 0 1 0 0 0 0 0999 V2000 3.3147 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7788 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9128 -0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7788 0.6636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7788 -0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2788 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6449 1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 -1.7213 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 13 2 0 0 0 0 4 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 1 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	2.922
LogD:	2.825
LogS:	-3.762
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	4.621
Fsp3:	0.6
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:	-5.088
MDCK Permeability:	1.9060580598306842e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.746
Plasma Protein Binding (PPB):	93.61368560791016%
Volume Distribution (VD):	1.289
Pgp-substrate:	6.827563285827637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.249
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.285
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.768
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	10.938
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.28
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.414
Carcinogencity:	0.105
Eye Corrosion:	0.004
Eye Irritation:	0.08
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC191521

Natural Product ID:	NPC191521
*Common Name:**	(E)-3-(2-((1R,5R,6R,8As)-6-Hydroxy-5-(Hydroxymethyl)-5,8A-Dimethyl-2-Methylenedecahydronaphthalen-1-Yl)Ethylidene)Furan-2(3H)-One
IUPAC Name:	(3E)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one
Synonyms:
Standard InCHIKey:	YIIRVUDGRKEWBV-FZOOCBFYSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5,9,11,15-17,21-22H,1,4,6-8,10,12H2,2-3H3/b14-5+/t15-,16+,17-,19+,20+/m1/s1
SMILES:	OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C/1C=COC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436162
PubChem CID:	6473762
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	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	16

Activity Type	# Activity
NON-MOLECULAR	3
Organism	4
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	19.0	%	PMID[556030]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	17.0	%	PMID[556030]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	18.0	%	PMID[556030]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	10.0	%	PMID[556030]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	16.0	%	PMID[556030]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.0	%	PMID[556030]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	13.0	%	PMID[556030]
NPT27	Others	Unspecified		Activity	=	15.55	%	PMID[556031]
NPT27	Others	Unspecified		Activity	=	1.57	%	PMID[556031]
NPT27	Others	Unspecified		Activity	=	0.3	%	PMID[556031]
NPT27	Others	Unspecified		Activity	=	82.58	%	PMID[556031]
NPT35	Others	n.a.		LogP	=	3.28	n.a.	PMID[556033]
NPT27	Others	Unspecified		K	=	12.74	/M/hr	PMID[556034]
NPT27	Others	Unspecified		Drug metabolism	>	95.0	%	PMID[556034]
NPT27	Others	Unspecified		T1/2	=	0.05	hr	PMID[556034]
NPT27	Others	Unspecified		Activity	>	70.0	%	PMID[556034]

☑ 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 NPC191521 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	181
0.1-0.2	957
0.2-0.3	3341
0.3-0.4	6419
0.4-0.5	15665
0.5-0.6	8725
0.6-0.7	5919
0.7-0.8	1321
0.8-0.85	130
0.85-0.9	28
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC16967
0.9659	High Similarity	NPC162615
0.9659	High Similarity	NPC152778
0.9659	High Similarity	NPC205034
0.9432	High Similarity	NPC310479
0.9213	High Similarity	NPC182136
0.914	High Similarity	NPC474440
0.913	High Similarity	NPC473153
0.9	High Similarity	NPC221111
0.9	High Similarity	NPC280149
0.8977	High Similarity	NPC131813
0.8901	High Similarity	NPC72845
0.8804	High Similarity	NPC139692
0.8791	High Similarity	NPC78973
0.8737	High Similarity	NPC278673
0.871	High Similarity	NPC470255
0.8636	High Similarity	NPC79945
0.8602	High Similarity	NPC472812
0.8586	High Similarity	NPC266570
0.8542	High Similarity	NPC57079
0.8542	High Similarity	NPC108368
0.8526	High Similarity	NPC242848
0.8526	High Similarity	NPC234993
0.8526	High Similarity	NPC134072
0.8511	High Similarity	NPC57117
0.8495	Intermediate Similarity	NPC472811
0.8478	Intermediate Similarity	NPC50488
0.8478	Intermediate Similarity	NPC474396
0.8469	Intermediate Similarity	NPC155332
0.8469	Intermediate Similarity	NPC114540
0.8469	Intermediate Similarity	NPC32577
0.8438	Intermediate Similarity	NPC73911
0.8427	Intermediate Similarity	NPC311070
0.8421	Intermediate Similarity	NPC276110
0.8421	Intermediate Similarity	NPC209355
0.8416	Intermediate Similarity	NPC275060
0.8404	Intermediate Similarity	NPC53555
0.84	Intermediate Similarity	NPC34768
0.84	Intermediate Similarity	NPC81630
0.8384	Intermediate Similarity	NPC171014
0.8351	Intermediate Similarity	NPC159763
0.8351	Intermediate Similarity	NPC278386
0.8351	Intermediate Similarity	NPC124512
0.8333	Intermediate Similarity	NPC75389
0.8333	Intermediate Similarity	NPC302360
0.8333	Intermediate Similarity	NPC190713
0.8317	Intermediate Similarity	NPC179380
0.8265	Intermediate Similarity	NPC474012
0.8265	Intermediate Similarity	NPC476299
0.8261	Intermediate Similarity	NPC473891
0.8247	Intermediate Similarity	NPC99726
0.8242	Intermediate Similarity	NPC109528
0.8242	Intermediate Similarity	NPC476602
0.8235	Intermediate Similarity	NPC137462
0.8235	Intermediate Similarity	NPC304276
0.8222	Intermediate Similarity	NPC57370
0.8218	Intermediate Similarity	NPC295843
0.8218	Intermediate Similarity	NPC189863
0.8218	Intermediate Similarity	NPC218158
0.8202	Intermediate Similarity	NPC159148
0.82	Intermediate Similarity	NPC23584
0.82	Intermediate Similarity	NPC45897
0.82	Intermediate Similarity	NPC297617
0.8182	Intermediate Similarity	NPC115899
0.8172	Intermediate Similarity	NPC472810
0.8172	Intermediate Similarity	NPC472809
0.8172	Intermediate Similarity	NPC104560
0.8163	Intermediate Similarity	NPC92275
0.8163	Intermediate Similarity	NPC473154
0.8163	Intermediate Similarity	NPC218107
0.8152	Intermediate Similarity	NPC329692
0.8144	Intermediate Similarity	NPC301534
0.8144	Intermediate Similarity	NPC260796
0.8144	Intermediate Similarity	NPC165632
0.8144	Intermediate Similarity	NPC250757
0.8137	Intermediate Similarity	NPC329048
0.8137	Intermediate Similarity	NPC330011
0.8137	Intermediate Similarity	NPC302788
0.8137	Intermediate Similarity	NPC79298
0.8137	Intermediate Similarity	NPC43063
0.8137	Intermediate Similarity	NPC475074
0.8132	Intermediate Similarity	NPC96055
0.8125	Intermediate Similarity	NPC105490
0.8105	Intermediate Similarity	NPC472814
0.8105	Intermediate Similarity	NPC329842
0.8105	Intermediate Similarity	NPC177037
0.81	Intermediate Similarity	NPC476081
0.81	Intermediate Similarity	NPC109195
0.81	Intermediate Similarity	NPC11956
0.81	Intermediate Similarity	NPC475038
0.8095	Intermediate Similarity	NPC44537
0.809	Intermediate Similarity	NPC281880
0.809	Intermediate Similarity	NPC268827
0.8085	Intermediate Similarity	NPC174342
0.8085	Intermediate Similarity	NPC314727
0.8085	Intermediate Similarity	NPC82876
0.8081	Intermediate Similarity	NPC266955
0.8081	Intermediate Similarity	NPC38855
0.8077	Intermediate Similarity	NPC12795
0.8068	Intermediate Similarity	NPC184737
0.8065	Intermediate Similarity	NPC166857
0.8061	Intermediate Similarity	NPC474343
0.8061	Intermediate Similarity	NPC110937
0.8061	Intermediate Similarity	NPC253826
0.8061	Intermediate Similarity	NPC141401
0.8061	Intermediate Similarity	NPC51499
0.8061	Intermediate Similarity	NPC208094
0.8043	Intermediate Similarity	NPC86316
0.8043	Intermediate Similarity	NPC106416
0.8043	Intermediate Similarity	NPC65661
0.8043	Intermediate Similarity	NPC471795
0.8043	Intermediate Similarity	NPC474013
0.8041	Intermediate Similarity	NPC472441
0.8041	Intermediate Similarity	NPC295347
0.8041	Intermediate Similarity	NPC183012
0.8039	Intermediate Similarity	NPC478208
0.8039	Intermediate Similarity	NPC471206
0.8022	Intermediate Similarity	NPC42476
0.8021	Intermediate Similarity	NPC7349
0.8021	Intermediate Similarity	NPC472641
0.8021	Intermediate Similarity	NPC214697
0.8021	Intermediate Similarity	NPC472640
0.802	Intermediate Similarity	NPC120321
0.802	Intermediate Similarity	NPC112009
0.802	Intermediate Similarity	NPC471938
0.8019	Intermediate Similarity	NPC241977
0.8	Intermediate Similarity	NPC194028
0.8	Intermediate Similarity	NPC472642
0.8	Intermediate Similarity	NPC303559
0.8	Intermediate Similarity	NPC282524
0.8	Intermediate Similarity	NPC170303
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC51486
0.8	Intermediate Similarity	NPC168319
0.7981	Intermediate Similarity	NPC475065
0.7981	Intermediate Similarity	NPC137911
0.7981	Intermediate Similarity	NPC228477
0.798	Intermediate Similarity	NPC316598
0.798	Intermediate Similarity	NPC275086
0.798	Intermediate Similarity	NPC325229
0.7979	Intermediate Similarity	NPC229612
0.7979	Intermediate Similarity	NPC93411
0.7979	Intermediate Similarity	NPC7280
0.7979	Intermediate Similarity	NPC473879
0.7961	Intermediate Similarity	NPC109376
0.7959	Intermediate Similarity	NPC471153
0.7955	Intermediate Similarity	NPC189206
0.7941	Intermediate Similarity	NPC471937
0.7938	Intermediate Similarity	NPC477129
0.7938	Intermediate Similarity	NPC477130
0.7938	Intermediate Similarity	NPC279410
0.7938	Intermediate Similarity	NPC119562
0.7938	Intermediate Similarity	NPC474690
0.7938	Intermediate Similarity	NPC201725
0.7938	Intermediate Similarity	NPC469697
0.7938	Intermediate Similarity	NPC476186
0.7935	Intermediate Similarity	NPC32223
0.7921	Intermediate Similarity	NPC471914
0.7921	Intermediate Similarity	NPC273668
0.7917	Intermediate Similarity	NPC212948
0.7912	Intermediate Similarity	NPC2524
0.7912	Intermediate Similarity	NPC471218
0.7912	Intermediate Similarity	NPC16321
0.7905	Intermediate Similarity	NPC16270
0.7905	Intermediate Similarity	NPC103491
0.7905	Intermediate Similarity	NPC478209
0.79	Intermediate Similarity	NPC201406
0.79	Intermediate Similarity	NPC471413
0.79	Intermediate Similarity	NPC16601
0.79	Intermediate Similarity	NPC47024
0.79	Intermediate Similarity	NPC227865
0.79	Intermediate Similarity	NPC117685
0.7895	Intermediate Similarity	NPC262858
0.7895	Intermediate Similarity	NPC470734
0.7895	Intermediate Similarity	NPC5509
0.7895	Intermediate Similarity	NPC146554
0.7895	Intermediate Similarity	NPC472240
0.7885	Intermediate Similarity	NPC473482
0.7885	Intermediate Similarity	NPC470024
0.7885	Intermediate Similarity	NPC475418
0.7885	Intermediate Similarity	NPC224660
0.7885	Intermediate Similarity	NPC50124
0.7885	Intermediate Similarity	NPC318363
0.7879	Intermediate Similarity	NPC2049
0.7879	Intermediate Similarity	NPC53844
0.7879	Intermediate Similarity	NPC205143
0.7879	Intermediate Similarity	NPC475709
0.7865	Intermediate Similarity	NPC476949
0.7864	Intermediate Similarity	NPC478052
0.7864	Intermediate Similarity	NPC477125
0.7864	Intermediate Similarity	NPC172867
0.7857	Intermediate Similarity	NPC88310
0.7857	Intermediate Similarity	NPC13924
0.7857	Intermediate Similarity	NPC180950
0.785	Intermediate Similarity	NPC171126
0.785	Intermediate Similarity	NPC73050
0.785	Intermediate Similarity	NPC154815
0.7849	Intermediate Similarity	NPC30984
0.7843	Intermediate Similarity	NPC72151
0.7843	Intermediate Similarity	NPC473283

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 NPC191521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1079
0.2-0.3	3311
0.3-0.4	2740
0.4-0.5	1325
0.5-0.6	307
0.6-0.7	215
0.7-0.8	14
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD4225	Approved
0.78	Intermediate Similarity	NPD7638	Approved
0.7723	Intermediate Similarity	NPD7640	Approved
0.7723	Intermediate Similarity	NPD7639	Approved
0.7717	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7637	Suspended
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD6686	Approved
0.7217	Intermediate Similarity	NPD7503	Approved
0.7212	Intermediate Similarity	NPD6648	Approved
0.72	Intermediate Similarity	NPD7515	Phase 2
0.7188	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5344	Discontinued
0.713	Intermediate Similarity	NPD5697	Approved
0.7113	Intermediate Similarity	NPD1694	Approved
0.71	Intermediate Similarity	NPD7838	Discovery
0.7075	Intermediate Similarity	NPD7632	Discontinued
0.7064	Intermediate Similarity	NPD6881	Approved
0.7064	Intermediate Similarity	NPD6899	Approved
0.7059	Intermediate Similarity	NPD7748	Approved
0.7041	Intermediate Similarity	NPD3618	Phase 1
0.703	Intermediate Similarity	NPD6079	Approved
0.703	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6961	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD8264	Approved
0.6937	Remote Similarity	NPD7290	Approved
0.6937	Remote Similarity	NPD7102	Approved
0.6937	Remote Similarity	NPD6883	Approved
0.6931	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5222	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6916	Remote Similarity	NPD5211	Phase 2
0.6909	Remote Similarity	NPD6011	Approved
0.6907	Remote Similarity	NPD6695	Phase 3
0.6887	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD5286	Approved
0.6887	Remote Similarity	NPD5285	Approved
0.6881	Remote Similarity	NPD6402	Approved
0.6881	Remote Similarity	NPD5739	Approved
0.6881	Remote Similarity	NPD7128	Approved
0.6881	Remote Similarity	NPD6675	Approved
0.6875	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD6869	Approved
0.6875	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD6649	Approved
0.6875	Remote Similarity	NPD6847	Approved
0.6857	Remote Similarity	NPD7902	Approved
0.6857	Remote Similarity	NPD5173	Approved
0.6848	Remote Similarity	NPD6924	Approved
0.6848	Remote Similarity	NPD6926	Approved
0.6842	Remote Similarity	NPD7645	Phase 2
0.6842	Remote Similarity	NPD6929	Approved
0.6837	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5328	Approved
0.6832	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD8297	Approved
0.6814	Remote Similarity	NPD6882	Approved
0.6813	Remote Similarity	NPD7151	Approved
0.6813	Remote Similarity	NPD7152	Approved
0.6813	Remote Similarity	NPD7150	Approved
0.681	Remote Similarity	NPD7328	Approved
0.681	Remote Similarity	NPD7327	Approved
0.6804	Remote Similarity	NPD5209	Approved
0.6804	Remote Similarity	NPD3667	Approved
0.6796	Remote Similarity	NPD6399	Phase 3
0.6789	Remote Similarity	NPD5141	Approved
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8033	Approved
0.6771	Remote Similarity	NPD6931	Approved
0.6771	Remote Similarity	NPD6930	Phase 2
0.6771	Remote Similarity	NPD7525	Registered
0.6771	Remote Similarity	NPD4695	Discontinued
0.6771	Remote Similarity	NPD7514	Phase 3
0.6771	Remote Similarity	NPD7332	Phase 2
0.6759	Remote Similarity	NPD5224	Approved
0.6759	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD4633	Approved
0.6757	Remote Similarity	NPD7320	Approved
0.6752	Remote Similarity	NPD7516	Approved
0.6737	Remote Similarity	NPD7145	Approved
0.6737	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7154	Phase 3
0.6703	Remote Similarity	NPD7144	Approved
0.6703	Remote Similarity	NPD7143	Approved
0.6702	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6933	Approved
0.6701	Remote Similarity	NPD6902	Approved
0.67	Remote Similarity	NPD5279	Phase 3
0.6698	Remote Similarity	NPD6083	Phase 2
0.6698	Remote Similarity	NPD6084	Phase 2
0.6698	Remote Similarity	NPD4755	Approved
0.6697	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6695	Remote Similarity	NPD8294	Approved
0.6695	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD4786	Approved
0.6639	Remote Similarity	NPD8379	Approved
0.6639	Remote Similarity	NPD8335	Approved
0.6639	Remote Similarity	NPD8380	Approved
0.6639	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD8296	Approved
0.6636	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4202	Approved
0.6634	Remote Similarity	NPD7524	Approved
0.6634	Remote Similarity	NPD7750	Discontinued
0.6634	Remote Similarity	NPD3573	Approved
0.6632	Remote Similarity	NPD6925	Approved
0.6632	Remote Similarity	NPD5776	Phase 2
0.6632	Remote Similarity	NPD6932	Approved
0.6609	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.66	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1696	Phase 3
0.6598	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7509	Discontinued
0.6596	Remote Similarity	NPD7339	Approved
0.6596	Remote Similarity	NPD6942	Approved
0.6593	Remote Similarity	NPD6923	Approved
0.6593	Remote Similarity	NPD6922	Approved
0.6574	Remote Similarity	NPD4700	Approved
0.6571	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7507	Approved
0.6538	Remote Similarity	NPD5284	Approved
0.6538	Remote Similarity	NPD5281	Approved
0.6535	Remote Similarity	NPD7334	Approved
0.6535	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD7146	Approved
0.6535	Remote Similarity	NPD7521	Approved
0.6535	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5210	Approved
0.6509	Remote Similarity	NPD4629	Approved
0.6509	Remote Similarity	NPD5695	Phase 3
0.6505	Remote Similarity	NPD4753	Phase 2
0.6496	Remote Similarity	NPD6868	Approved
0.6496	Remote Similarity	NPD6274	Approved
0.6495	Remote Similarity	NPD4195	Approved
0.6481	Remote Similarity	NPD5290	Discontinued
0.6481	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.646	Remote Similarity	NPD4729	Approved
0.646	Remote Similarity	NPD4730	Approved
0.6442	Remote Similarity	NPD46	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6441	Remote Similarity	NPD6009	Approved
0.6441	Remote Similarity	NPD6317	Approved
0.6436	Remote Similarity	NPD5363	Approved
0.6436	Remote Similarity	NPD6893	Approved
0.6435	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4819	Approved
0.6429	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD8039	Approved
0.6417	Remote Similarity	NPD6319	Approved
0.6408	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6672	Approved
0.6408	Remote Similarity	NPD6903	Approved
0.6408	Remote Similarity	NPD5737	Approved
0.64	Remote Similarity	NPD5362	Discontinued
0.64	Remote Similarity	NPD7319	Approved
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4271	Approved
0.6392	Remote Similarity	NPD4268	Approved
0.6387	Remote Similarity	NPD6313	Approved
0.6387	Remote Similarity	NPD6314	Approved
0.6387	Remote Similarity	NPD6335	Approved
0.6381	Remote Similarity	NPD7087	Discontinued
0.6381	Remote Similarity	NPD5693	Phase 1
0.6381	Remote Similarity	NPD8035	Phase 2
0.6381	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4249	Approved
0.6373	Remote Similarity	NPD4519	Discontinued
0.6373	Remote Similarity	NPD4623	Approved
0.6364	Remote Similarity	NPD6898	Phase 1

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