NPASS Compound

Structure

NPC474440 OpenBabel07101718222D 26 28 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 0.9013 -1.8841 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 -5.0468 -0.6636 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 -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 -0.5000 -0.8660 0.0000 C 0 0 3 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 -6.7788 2.0685 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 -0.0933 -1.7796 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 25 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 1 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 21 1 1 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 2 1 1 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	379.508
LogP:	2.871
LogD:	3.017
LogS:	-4.122
# Rotatable Bonds:	4
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	4.762
Fsp3:	0.619
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:	-4.909
MDCK Permeability:	1.7558166291564703e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.252
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.134

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	86.03472137451172%
Volume Distribution (VD):	0.805
Pgp-substrate:	14.61180591583252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.603
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.659
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.568
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.846
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	9.527
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.445
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.576
Carcinogencity:	0.048
Eye Corrosion:	0.007
Eye Irritation:	0.125
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC474440

Natural Product ID:	NPC474440
*Common Name:**	3-(2-((1R,4As,5R,6R,8Ar)-6-Hydroxy-5-(Hydroxymethyl)-5,8A-Dimethyl-2-Methylene-Decahydronaphthalen-1-Yl)Vinyl)-5-Methoxyfuran-2(5H)-One
IUPAC Name:	4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-methoxy-2H-furan-5-one
Synonyms:
Standard InCHIKey:	CNXJVKMKGPSCDO-ZPBQUNJGSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-13-5-8-16-20(2,10-9-17(23)21(16,3)12-22)15(13)7-6-14-11-18(25-4)26-19(14)24/h6-7,11,15-18,22-23H,1,5,8-10,12H2,2-4H3/b7-6+/t15-,16+,17-,18?,20+,21+/m1/s1
SMILES:	COC1OC(=O)C(=C1)/C=C/[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@H]([C@@]2(C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468575
PubChem CID:	44577207
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
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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	26360.0	nM	PMID[532769]

☑ 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 NPC474440 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	191
0.1-0.2	1037
0.2-0.3	3700
0.3-0.4	7433
0.4-0.5	14480
0.5-0.6	7992
0.6-0.7	6288
0.7-0.8	1370
0.8-0.85	170
0.85-0.9	25
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9451	High Similarity	NPC152778
0.9451	High Similarity	NPC205034
0.9451	High Similarity	NPC162615
0.9348	High Similarity	NPC470255
0.9239	High Similarity	NPC472812
0.9231	High Similarity	NPC310479
0.9149	High Similarity	NPC16967
0.914	High Similarity	NPC191521
0.913	High Similarity	NPC472811
0.9022	High Similarity	NPC182136
0.899	High Similarity	NPC218158
0.8958	High Similarity	NPC473154
0.8947	High Similarity	NPC473153
0.8817	High Similarity	NPC280149
0.8817	High Similarity	NPC221111
0.8804	High Similarity	NPC472809
0.8804	High Similarity	NPC472810
0.8791	High Similarity	NPC131813
0.8723	High Similarity	NPC72845
0.8713	High Similarity	NPC109376
0.8646	High Similarity	NPC472441
0.8632	High Similarity	NPC139692
0.8627	High Similarity	NPC470024
0.8627	High Similarity	NPC224660
0.8617	High Similarity	NPC78973
0.8614	High Similarity	NPC172867
0.86	High Similarity	NPC45897
0.86	High Similarity	NPC134270
0.8542	High Similarity	NPC469697
0.8515	High Similarity	NPC201880
0.8515	High Similarity	NPC473207
0.8515	High Similarity	NPC81567
0.8515	High Similarity	NPC264867
0.8515	High Similarity	NPC470321
0.8511	High Similarity	NPC470734
0.85	High Similarity	NPC238397
0.85	High Similarity	NPC471363
0.8469	Intermediate Similarity	NPC475709
0.8462	Intermediate Similarity	NPC316708
0.8454	Intermediate Similarity	NPC13924
0.8431	Intermediate Similarity	NPC252296
0.8431	Intermediate Similarity	NPC82251
0.8416	Intermediate Similarity	NPC127933
0.8416	Intermediate Similarity	NPC7644
0.8416	Intermediate Similarity	NPC7613
0.8416	Intermediate Similarity	NPC120009
0.8416	Intermediate Similarity	NPC475889
0.8404	Intermediate Similarity	NPC474629
0.84	Intermediate Similarity	NPC198992
0.8381	Intermediate Similarity	NPC470026
0.8381	Intermediate Similarity	NPC17791
0.8367	Intermediate Similarity	NPC234993
0.8367	Intermediate Similarity	NPC162346
0.8367	Intermediate Similarity	NPC165632
0.8367	Intermediate Similarity	NPC242848
0.8367	Intermediate Similarity	NPC134072
0.8351	Intermediate Similarity	NPC57117
0.8351	Intermediate Similarity	NPC298973
0.8351	Intermediate Similarity	NPC104925
0.835	Intermediate Similarity	NPC184512
0.835	Intermediate Similarity	NPC475074
0.8333	Intermediate Similarity	NPC329842
0.8333	Intermediate Similarity	NPC477783
0.8333	Intermediate Similarity	NPC471937
0.8317	Intermediate Similarity	NPC114540
0.8317	Intermediate Similarity	NPC32577
0.8317	Intermediate Similarity	NPC121423
0.8317	Intermediate Similarity	NPC155332
0.8317	Intermediate Similarity	NPC472815
0.8316	Intermediate Similarity	NPC474396
0.8316	Intermediate Similarity	NPC50488
0.8302	Intermediate Similarity	NPC328074
0.8302	Intermediate Similarity	NPC470025
0.8302	Intermediate Similarity	NPC321272
0.8302	Intermediate Similarity	NPC317460
0.83	Intermediate Similarity	NPC324841
0.83	Intermediate Similarity	NPC477720
0.8283	Intermediate Similarity	NPC73911
0.8269	Intermediate Similarity	NPC311223
0.8265	Intermediate Similarity	NPC209355
0.8265	Intermediate Similarity	NPC276110
0.8261	Intermediate Similarity	NPC311070
0.8261	Intermediate Similarity	NPC79945
0.8247	Intermediate Similarity	NPC53555
0.8247	Intermediate Similarity	NPC472641
0.8247	Intermediate Similarity	NPC472640
0.8235	Intermediate Similarity	NPC471938
0.8229	Intermediate Similarity	NPC472642
0.8229	Intermediate Similarity	NPC477782
0.8224	Intermediate Similarity	NPC470027
0.8211	Intermediate Similarity	NPC472378
0.82	Intermediate Similarity	NPC278386
0.82	Intermediate Similarity	NPC124512
0.82	Intermediate Similarity	NPC57079
0.82	Intermediate Similarity	NPC159763
0.82	Intermediate Similarity	NPC278673
0.82	Intermediate Similarity	NPC108368
0.819	Intermediate Similarity	NPC316974
0.819	Intermediate Similarity	NPC206618
0.8173	Intermediate Similarity	NPC88013
0.8173	Intermediate Similarity	NPC125423
0.8163	Intermediate Similarity	NPC474554
0.8137	Intermediate Similarity	NPC471914
0.8125	Intermediate Similarity	NPC251528
0.8119	Intermediate Similarity	NPC473204
0.8119	Intermediate Similarity	NPC16601
0.8119	Intermediate Similarity	NPC474012
0.8119	Intermediate Similarity	NPC476299
0.8119	Intermediate Similarity	NPC477716
0.8119	Intermediate Similarity	NPC477721
0.8113	Intermediate Similarity	NPC177047
0.8113	Intermediate Similarity	NPC119550
0.8105	Intermediate Similarity	NPC473891
0.81	Intermediate Similarity	NPC477719
0.81	Intermediate Similarity	NPC98112
0.81	Intermediate Similarity	NPC477718
0.81	Intermediate Similarity	NPC472188
0.8095	Intermediate Similarity	NPC128795
0.8095	Intermediate Similarity	NPC48548
0.8095	Intermediate Similarity	NPC135015
0.8095	Intermediate Similarity	NPC217921
0.8095	Intermediate Similarity	NPC38948
0.8091	Intermediate Similarity	NPC473828
0.8091	Intermediate Similarity	NPC473617
0.8085	Intermediate Similarity	NPC476602
0.8085	Intermediate Similarity	NPC473251
0.8085	Intermediate Similarity	NPC329630
0.8085	Intermediate Similarity	NPC42586
0.8081	Intermediate Similarity	NPC471362
0.8081	Intermediate Similarity	NPC471372
0.8081	Intermediate Similarity	NPC472189
0.8077	Intermediate Similarity	NPC266570
0.8077	Intermediate Similarity	NPC239961
0.8058	Intermediate Similarity	NPC23584
0.8058	Intermediate Similarity	NPC471364
0.8058	Intermediate Similarity	NPC471365
0.8058	Intermediate Similarity	NPC297617
0.8058	Intermediate Similarity	NPC132395
0.8056	Intermediate Similarity	NPC264153
0.8041	Intermediate Similarity	NPC469403
0.8041	Intermediate Similarity	NPC253186
0.8039	Intermediate Similarity	NPC115899
0.8039	Intermediate Similarity	NPC477717
0.802	Intermediate Similarity	NPC472186
0.802	Intermediate Similarity	NPC471366
0.802	Intermediate Similarity	NPC318917
0.802	Intermediate Similarity	NPC476800
0.802	Intermediate Similarity	NPC92275
0.8019	Intermediate Similarity	NPC40728
0.8	Intermediate Similarity	NPC17578
0.8	Intermediate Similarity	NPC171598
0.8	Intermediate Similarity	NPC190713
0.8	Intermediate Similarity	NPC329692
0.8	Intermediate Similarity	NPC240673
0.7982	Intermediate Similarity	NPC475163
0.798	Intermediate Similarity	NPC105490
0.7979	Intermediate Similarity	NPC302360
0.7979	Intermediate Similarity	NPC96055
0.7979	Intermediate Similarity	NPC471302
0.7979	Intermediate Similarity	NPC470800
0.7961	Intermediate Similarity	NPC476081
0.7961	Intermediate Similarity	NPC11956
0.7961	Intermediate Similarity	NPC470571
0.7961	Intermediate Similarity	NPC109195
0.7961	Intermediate Similarity	NPC475038
0.7959	Intermediate Similarity	NPC472814
0.7959	Intermediate Similarity	NPC177037
0.7959	Intermediate Similarity	NPC141831
0.7959	Intermediate Similarity	NPC78594
0.7941	Intermediate Similarity	NPC477972
0.7941	Intermediate Similarity	NPC477968
0.7941	Intermediate Similarity	NPC477971
0.7941	Intermediate Similarity	NPC472187
0.7941	Intermediate Similarity	NPC266955
0.7941	Intermediate Similarity	NPC38855
0.7941	Intermediate Similarity	NPC20113
0.7941	Intermediate Similarity	NPC228251
0.7941	Intermediate Similarity	NPC473545
0.7941	Intermediate Similarity	NPC219285
0.7941	Intermediate Similarity	NPC161527
0.7938	Intermediate Similarity	NPC174342
0.7938	Intermediate Similarity	NPC82876
0.7935	Intermediate Similarity	NPC10636
0.7935	Intermediate Similarity	NPC268827
0.7925	Intermediate Similarity	NPC392
0.7925	Intermediate Similarity	NPC219900
0.7925	Intermediate Similarity	NPC177524
0.7925	Intermediate Similarity	NPC181994
0.7921	Intermediate Similarity	NPC110937
0.7921	Intermediate Similarity	NPC474343
0.7921	Intermediate Similarity	NPC141401
0.7921	Intermediate Similarity	NPC51499
0.7921	Intermediate Similarity	NPC99726
0.7917	Intermediate Similarity	NPC166857
0.7912	Intermediate Similarity	NPC184737
0.7909	Intermediate Similarity	NPC471816
0.7905	Intermediate Similarity	NPC81630
0.7905	Intermediate Similarity	NPC34768
0.79	Intermediate Similarity	NPC183012
0.79	Intermediate Similarity	NPC471915

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 NPC474440 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1180
0.2-0.3	3442
0.3-0.4	2731
0.4-0.5	1146
0.5-0.6	261
0.6-0.7	210
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
0.82	Intermediate Similarity	NPD4225	Approved
0.7925	Intermediate Similarity	NPD6686	Approved
0.7789	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7638	Approved
0.7596	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD7640	Approved
0.7579	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7503	Approved
0.7456	Intermediate Similarity	NPD7327	Approved
0.7456	Intermediate Similarity	NPD7328	Approved
0.7414	Intermediate Similarity	NPD8033	Approved
0.7391	Intermediate Similarity	NPD7516	Approved
0.7328	Intermediate Similarity	NPD8294	Approved
0.7328	Intermediate Similarity	NPD8377	Approved
0.7265	Intermediate Similarity	NPD8296	Approved
0.7265	Intermediate Similarity	NPD8380	Approved
0.7265	Intermediate Similarity	NPD8335	Approved
0.7265	Intermediate Similarity	NPD8379	Approved
0.7265	Intermediate Similarity	NPD8378	Approved
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7168	Intermediate Similarity	NPD6882	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7103	Intermediate Similarity	NPD6648	Approved
0.7037	Intermediate Similarity	NPD5344	Discontinued
0.7027	Intermediate Similarity	NPD5697	Approved
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1694	Approved
0.6992	Remote Similarity	NPD7319	Approved
0.699	Remote Similarity	NPD7838	Discovery
0.6972	Remote Similarity	NPD7632	Discontinued
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6952	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.6923	Remote Similarity	NPD7515	Phase 2
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6814	Remote Similarity	NPD6011	Approved
0.68	Remote Similarity	NPD6695	Phase 3
0.6786	Remote Similarity	NPD5739	Approved
0.6786	Remote Similarity	NPD6675	Approved
0.6786	Remote Similarity	NPD7128	Approved
0.6786	Remote Similarity	NPD6402	Approved
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6649	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6765	Remote Similarity	NPD3618	Phase 1
0.6762	Remote Similarity	NPD6079	Approved
0.6759	Remote Similarity	NPD7902	Approved
0.6733	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6101	Approved
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD5701	Approved
0.6724	Remote Similarity	NPD8297	Approved
0.67	Remote Similarity	NPD5209	Approved
0.6698	Remote Similarity	NPD6399	Phase 3
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.664	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6009	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6609	Remote Similarity	NPD6372	Approved
0.6609	Remote Similarity	NPD6373	Approved
0.6606	Remote Similarity	NPD6083	Phase 2
0.6606	Remote Similarity	NPD6084	Phase 2
0.6606	Remote Similarity	NPD5173	Approved
0.6571	Remote Similarity	NPD6051	Approved
0.6571	Remote Similarity	NPD5328	Approved
0.6566	Remote Similarity	NPD6929	Approved
0.6566	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD6924	Approved
0.6562	Remote Similarity	NPD6926	Approved
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8516	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6549	Remote Similarity	NPD5141	Approved
0.6538	Remote Similarity	NPD7524	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6538	Remote Similarity	NPD7750	Discontinued
0.6535	Remote Similarity	NPD3667	Approved
0.6532	Remote Similarity	NPD7492	Approved
0.6526	Remote Similarity	NPD7152	Approved
0.6526	Remote Similarity	NPD7151	Approved
0.6526	Remote Similarity	NPD7150	Approved
0.6525	Remote Similarity	NPD8133	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD7332	Phase 2
0.65	Remote Similarity	NPD6931	Approved
0.65	Remote Similarity	NPD7525	Registered
0.65	Remote Similarity	NPD7514	Phase 3
0.65	Remote Similarity	NPD6930	Phase 2
0.6481	Remote Similarity	NPD7900	Approved
0.6481	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6616	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6466	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7145	Approved
0.6465	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD8328	Phase 3
0.6442	Remote Similarity	NPD5330	Approved
0.6442	Remote Similarity	NPD7334	Approved
0.6442	Remote Similarity	NPD5279	Phase 3
0.6442	Remote Similarity	NPD6409	Approved
0.6442	Remote Similarity	NPD7146	Approved
0.6442	Remote Similarity	NPD7521	Approved
0.6442	Remote Similarity	NPD6684	Approved
0.6436	Remote Similarity	NPD6902	Approved
0.6435	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6933	Approved
0.6429	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD6015	Approved
0.6423	Remote Similarity	NPD6016	Approved
0.6422	Remote Similarity	NPD5695	Phase 3
0.6421	Remote Similarity	NPD7143	Approved
0.6421	Remote Similarity	NPD7144	Approved
0.6417	Remote Similarity	NPD6274	Approved
0.6417	Remote Similarity	NPD6868	Approved
0.6408	Remote Similarity	NPD3666	Approved
0.6408	Remote Similarity	NPD4786	Approved
0.6408	Remote Similarity	NPD3133	Approved
0.6408	Remote Similarity	NPD3665	Phase 1
0.6396	Remote Similarity	NPD5696	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6389	Remote Similarity	NPD4202	Approved
0.6387	Remote Similarity	NPD4632	Approved
0.6371	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6925	Approved
0.6364	Remote Similarity	NPD5776	Phase 2
0.6364	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD6932	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6356	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD46	Approved
0.6355	Remote Similarity	NPD6698	Approved
0.6346	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1696	Phase 3
0.6341	Remote Similarity	NPD6319	Approved
0.6339	Remote Similarity	NPD4700	Approved
0.6337	Remote Similarity	NPD7509	Discontinued
0.6337	Remote Similarity	NPD4695	Discontinued
0.6337	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6942	Approved
0.6327	Remote Similarity	NPD7339	Approved
0.6327	Remote Similarity	NPD8039	Approved
0.6321	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6672	Approved
0.6321	Remote Similarity	NPD5737	Approved
0.6321	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD6922	Approved
0.6316	Remote Similarity	NPD6923	Approved
0.6311	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD7154	Phase 3
0.6311	Remote Similarity	NPD6313	Approved
0.6311	Remote Similarity	NPD6314	Approved
0.6296	Remote Similarity	NPD5284	Approved
0.6296	Remote Similarity	NPD8034	Phase 2
0.6296	Remote Similarity	NPD5281	Approved
0.6296	Remote Similarity	NPD8035	Phase 2
0.6296	Remote Similarity	NPD5693	Phase 1
0.6296	Remote Similarity	NPD7087	Discontinued
0.6273	Remote Similarity	NPD5210	Approved
0.6273	Remote Similarity	NPD4629	Approved
0.6262	Remote Similarity	NPD4753	Phase 2
0.6262	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5290	Discontinued
0.6239	Remote Similarity	NPD4729	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