NPASS Compound

Structure

CID159763 OpenBabel06191715532D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.4487 -3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9128 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -3.8364 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 -2.4487 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -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 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 -6.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -3.3364 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 -3.3147 -2.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.0468 -2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9128 -0.8364 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 -4.1808 -1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9128 -1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9128 -3.5685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2213 1.3272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -0.3364 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 12 2 0 0 0 0 4 7 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 25 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 6 0 0 0 15 22 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	364.849
LogP:	1.722
LogD:	1.02
LogS:	-2.784
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	4.942
Fsp3:	0.75
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:	-4.834
MDCK Permeability:	4.074126263731159e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.205
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.844
Plasma Protein Binding (PPB):	33.315147399902344%
Volume Distribution (VD):	0.568
Pgp-substrate:	60.25072479248047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.497
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	4.844
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.689
Rat Oral Acute Toxicity:	0.453
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.111
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.319

Download Data

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

Natural Product: NPC159763

Natural Product ID:	NPC159763
*Common Name:**	Isoandrographolide
IUPAC Name:	(3Z)-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]-4-hydroxyoxolan-2-one
Synonyms:	Isoandrographolide
Standard InCHIKey:	BOJKULTULYSRAS-OTVACULJSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5-/t14-,15?,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=C1/C(O)COC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479285
PubChem CID:	11078630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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]
NPO3876	Andrographis elongata	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]
NPO3876	Andrographis elongata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	7.0	mm	PMID[475784]

☑ 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 NPC159763 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	183
0.1-0.2	1027
0.2-0.3	3638
0.3-0.4	6845
0.4-0.5	14094
0.5-0.6	6828
0.6-0.7	6896
0.7-0.8	2964
0.8-0.85	189
0.85-0.9	21
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124512
1.0	High Similarity	NPC278386
0.9674	High Similarity	NPC73911
0.9341	High Similarity	NPC72845
0.914	High Similarity	NPC57117
0.9121	High Similarity	NPC474396
0.9121	High Similarity	NPC79027
0.9121	High Similarity	NPC50488
0.8947	High Similarity	NPC242848
0.883	High Similarity	NPC53555
0.8791	High Similarity	NPC329692
0.8776	High Similarity	NPC303559
0.875	High Similarity	NPC264153
0.875	High Similarity	NPC473153
0.866	High Similarity	NPC474343
0.8632	High Similarity	NPC152778
0.8632	High Similarity	NPC162615
0.8632	High Similarity	NPC205034
0.8632	High Similarity	NPC139692
0.8617	High Similarity	NPC78973
0.8587	High Similarity	NPC131813
0.8571	High Similarity	NPC473154
0.8557	High Similarity	NPC234993
0.8557	High Similarity	NPC134072
0.8529	High Similarity	NPC67321
0.8529	High Similarity	NPC187435
0.8526	High Similarity	NPC472814
0.8526	High Similarity	NPC177037
0.8515	High Similarity	NPC296950
0.8515	High Similarity	NPC146731
0.8495	Intermediate Similarity	NPC473891
0.8485	Intermediate Similarity	NPC38855
0.8485	Intermediate Similarity	NPC474012
0.8485	Intermediate Similarity	NPC476299
0.8478	Intermediate Similarity	NPC476602
0.8476	Intermediate Similarity	NPC269530
0.8454	Intermediate Similarity	NPC183012
0.8447	Intermediate Similarity	NPC306265
0.8438	Intermediate Similarity	NPC472812
0.8421	Intermediate Similarity	NPC182136
0.8421	Intermediate Similarity	NPC310479
0.8416	Intermediate Similarity	NPC159533
0.8384	Intermediate Similarity	NPC316598
0.8367	Intermediate Similarity	NPC16967
0.8365	Intermediate Similarity	NPC475065
0.8351	Intermediate Similarity	NPC191521
0.835	Intermediate Similarity	NPC330011
0.835	Intermediate Similarity	NPC329048
0.8333	Intermediate Similarity	NPC470493
0.8333	Intermediate Similarity	NPC140055
0.8333	Intermediate Similarity	NPC472811
0.8333	Intermediate Similarity	NPC470492
0.8333	Intermediate Similarity	NPC20302
0.8333	Intermediate Similarity	NPC167606
0.8333	Intermediate Similarity	NPC312824
0.8333	Intermediate Similarity	NPC286528
0.8333	Intermediate Similarity	NPC183580
0.8318	Intermediate Similarity	NPC67259
0.8318	Intermediate Similarity	NPC147912
0.8317	Intermediate Similarity	NPC472815
0.8316	Intermediate Similarity	NPC82876
0.83	Intermediate Similarity	NPC47024
0.8298	Intermediate Similarity	NPC166857
0.8286	Intermediate Similarity	NPC235014
0.8283	Intermediate Similarity	NPC475709
0.8283	Intermediate Similarity	NPC287668
0.8269	Intermediate Similarity	NPC475418
0.8269	Intermediate Similarity	NPC473482
0.8269	Intermediate Similarity	NPC318363
0.8261	Intermediate Similarity	NPC311070
0.8261	Intermediate Similarity	NPC79945
0.8257	Intermediate Similarity	NPC50774
0.8257	Intermediate Similarity	NPC709
0.8252	Intermediate Similarity	NPC477125
0.8247	Intermediate Similarity	NPC115021
0.8235	Intermediate Similarity	NPC476237
0.8235	Intermediate Similarity	NPC471938
0.8229	Intermediate Similarity	NPC221111
0.8229	Intermediate Similarity	NPC280149
0.8229	Intermediate Similarity	NPC51486
0.8218	Intermediate Similarity	NPC308824
0.8211	Intermediate Similarity	NPC104560
0.82	Intermediate Similarity	NPC474440
0.819	Intermediate Similarity	NPC474243
0.8182	Intermediate Similarity	NPC264954
0.8173	Intermediate Similarity	NPC473284
0.8163	Intermediate Similarity	NPC470697
0.8155	Intermediate Similarity	NPC471937
0.8144	Intermediate Similarity	NPC186363
0.8144	Intermediate Similarity	NPC233345
0.8137	Intermediate Similarity	NPC471914
0.8137	Intermediate Similarity	NPC273668
0.8137	Intermediate Similarity	NPC283343
0.8137	Intermediate Similarity	NPC476081
0.8137	Intermediate Similarity	NPC258547
0.8125	Intermediate Similarity	NPC77001
0.8125	Intermediate Similarity	NPC253618
0.8119	Intermediate Similarity	NPC117685
0.8113	Intermediate Similarity	NPC478211
0.8113	Intermediate Similarity	NPC5103
0.8108	Intermediate Similarity	NPC474370
0.8105	Intermediate Similarity	NPC181103
0.81	Intermediate Similarity	NPC253826
0.81	Intermediate Similarity	NPC205143
0.8095	Intermediate Similarity	NPC181994
0.8095	Intermediate Similarity	NPC38948
0.8095	Intermediate Similarity	NPC37628
0.8091	Intermediate Similarity	NPC186525
0.8091	Intermediate Similarity	NPC478206
0.8091	Intermediate Similarity	NPC478205
0.8091	Intermediate Similarity	NPC108581
0.8085	Intermediate Similarity	NPC35933
0.8081	Intermediate Similarity	NPC276110
0.8081	Intermediate Similarity	NPC476519
0.8081	Intermediate Similarity	NPC209355
0.8077	Intermediate Similarity	NPC88349
0.8073	Intermediate Similarity	NPC470075
0.8073	Intermediate Similarity	NPC64318
0.8061	Intermediate Similarity	NPC469645
0.8061	Intermediate Similarity	NPC469692
0.8058	Intermediate Similarity	NPC156681
0.8058	Intermediate Similarity	NPC72842
0.8058	Intermediate Similarity	NPC475050
0.8058	Intermediate Similarity	NPC99510
0.8058	Intermediate Similarity	NPC120321
0.8056	Intermediate Similarity	NPC477126
0.8056	Intermediate Similarity	NPC122056
0.8056	Intermediate Similarity	NPC478212
0.8043	Intermediate Similarity	NPC159148
0.8043	Intermediate Similarity	NPC170303
0.8039	Intermediate Similarity	NPC473160
0.8037	Intermediate Similarity	NPC100329
0.8037	Intermediate Similarity	NPC474315
0.8037	Intermediate Similarity	NPC247031
0.8037	Intermediate Similarity	NPC132790
0.8037	Intermediate Similarity	NPC97939
0.8036	Intermediate Similarity	NPC67569
0.8021	Intermediate Similarity	NPC472809
0.8021	Intermediate Similarity	NPC472810
0.802	Intermediate Similarity	NPC216478
0.802	Intermediate Similarity	NPC478056
0.802	Intermediate Similarity	NPC278008
0.802	Intermediate Similarity	NPC218107
0.8019	Intermediate Similarity	NPC42662
0.8019	Intermediate Similarity	NPC206618
0.8	Intermediate Similarity	NPC114743
0.8	Intermediate Similarity	NPC301666
0.8	Intermediate Similarity	NPC175145
0.8	Intermediate Similarity	NPC53396
0.8	Intermediate Similarity	NPC195366
0.8	Intermediate Similarity	NPC88009
0.8	Intermediate Similarity	NPC475176
0.8	Intermediate Similarity	NPC202833
0.8	Intermediate Similarity	NPC98249
0.8	Intermediate Similarity	NPC78966
0.8	Intermediate Similarity	NPC131665
0.8	Intermediate Similarity	NPC165632
0.8	Intermediate Similarity	NPC473656
0.8	Intermediate Similarity	NPC255387
0.8	Intermediate Similarity	NPC469684
0.8	Intermediate Similarity	NPC58662
0.8	Intermediate Similarity	NPC475069
0.8	Intermediate Similarity	NPC284732
0.8	Intermediate Similarity	NPC473968
0.8	Intermediate Similarity	NPC478204
0.7982	Intermediate Similarity	NPC8369
0.798	Intermediate Similarity	NPC121825
0.798	Intermediate Similarity	NPC24861
0.798	Intermediate Similarity	NPC470255
0.7979	Intermediate Similarity	NPC96055
0.7965	Intermediate Similarity	NPC153700
0.7965	Intermediate Similarity	NPC88326
0.7965	Intermediate Similarity	NPC470265
0.7965	Intermediate Similarity	NPC23786
0.7963	Intermediate Similarity	NPC69291
0.7963	Intermediate Similarity	NPC470063
0.7963	Intermediate Similarity	NPC476801
0.7961	Intermediate Similarity	NPC164551
0.7961	Intermediate Similarity	NPC472552
0.7961	Intermediate Similarity	NPC58329
0.7961	Intermediate Similarity	NPC109195
0.7961	Intermediate Similarity	NPC155332
0.7961	Intermediate Similarity	NPC475038
0.7961	Intermediate Similarity	NPC32577
0.7961	Intermediate Similarity	NPC114540
0.7961	Intermediate Similarity	NPC295791
0.7959	Intermediate Similarity	NPC303697
0.7959	Intermediate Similarity	NPC329842
0.7944	Intermediate Similarity	NPC29133
0.7944	Intermediate Similarity	NPC478209
0.7941	Intermediate Similarity	NPC473510
0.7941	Intermediate Similarity	NPC474190
0.7941	Intermediate Similarity	NPC476303
0.7941	Intermediate Similarity	NPC251680
0.7938	Intermediate Similarity	NPC314727
0.7938	Intermediate Similarity	NPC218927
0.7938	Intermediate Similarity	NPC168131
0.7938	Intermediate Similarity	NPC174342
0.7938	Intermediate Similarity	NPC206001
0.7938	Intermediate Similarity	NPC246028

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 NPC159763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1256
0.2-0.3	3536
0.3-0.4	2694
0.4-0.5	966
0.5-0.6	262
0.6-0.7	234
0.7-0.8	49
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4225	Approved
0.8333	Intermediate Similarity	NPD7115	Discovery
0.7941	Intermediate Similarity	NPD7640	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD6686	Approved
0.7579	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5344	Discontinued
0.7426	Intermediate Similarity	NPD7637	Suspended
0.7379	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1694	Approved
0.7327	Intermediate Similarity	NPD5785	Approved
0.7297	Intermediate Similarity	NPD6371	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7748	Approved
0.7103	Intermediate Similarity	NPD6648	Approved
0.71	Intermediate Similarity	NPD3618	Phase 1
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.7075	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6319	Approved
0.7027	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5697	Approved
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7019	Intermediate Similarity	NPD5778	Approved
0.7019	Intermediate Similarity	NPD5779	Approved
0.7018	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD7327	Approved
0.7009	Intermediate Similarity	NPD7328	Approved
0.6992	Remote Similarity	NPD7319	Approved
0.699	Remote Similarity	NPD6698	Approved
0.699	Remote Similarity	NPD46	Approved
0.699	Remote Similarity	NPD7838	Discovery
0.6975	Remote Similarity	NPD8033	Approved
0.6964	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6949	Remote Similarity	NPD7516	Approved
0.6937	Remote Similarity	NPD5739	Approved
0.6937	Remote Similarity	NPD6675	Approved
0.6937	Remote Similarity	NPD6402	Approved
0.6937	Remote Similarity	NPD7128	Approved
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6373	Approved
0.6903	Remote Similarity	NPD6372	Approved
0.6903	Remote Similarity	NPD6014	Approved
0.6891	Remote Similarity	NPD8377	Approved
0.6891	Remote Similarity	NPD8294	Approved
0.6885	Remote Similarity	NPD7507	Approved
0.6875	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5701	Approved
0.6863	Remote Similarity	NPD7524	Approved
0.6852	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6833	Remote Similarity	NPD8378	Approved
0.6833	Remote Similarity	NPD8335	Approved
0.6833	Remote Similarity	NPD7503	Approved
0.6833	Remote Similarity	NPD8379	Approved
0.6833	Remote Similarity	NPD8296	Approved
0.6833	Remote Similarity	NPD8380	Approved
0.6832	Remote Similarity	NPD5363	Approved
0.6818	Remote Similarity	NPD5211	Phase 2
0.6814	Remote Similarity	NPD6011	Approved
0.6814	Remote Similarity	NPD7320	Approved
0.681	Remote Similarity	NPD4632	Approved
0.6803	Remote Similarity	NPD7492	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6765	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6079	Approved
0.6759	Remote Similarity	NPD6084	Phase 2
0.6759	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD6054	Approved
0.6748	Remote Similarity	NPD6616	Approved
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6101	Approved
0.6731	Remote Similarity	NPD5328	Approved
0.6724	Remote Similarity	NPD6882	Approved
0.6721	Remote Similarity	NPD8328	Phase 3
0.67	Remote Similarity	NPD5209	Approved
0.67	Remote Similarity	NPD3667	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5222	Approved
0.664	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6637	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6634	Remote Similarity	NPD6695	Phase 3
0.6612	Remote Similarity	NPD6059	Approved
0.6606	Remote Similarity	NPD4755	Approved
0.6606	Remote Similarity	NPD5173	Approved
0.6604	Remote Similarity	NPD8035	Phase 2
0.6604	Remote Similarity	NPD8034	Phase 2
0.6604	Remote Similarity	NPD7983	Approved
0.6602	Remote Similarity	NPD7334	Approved
0.6602	Remote Similarity	NPD6684	Approved
0.6602	Remote Similarity	NPD6409	Approved
0.6602	Remote Similarity	NPD7521	Approved
0.6602	Remote Similarity	NPD5330	Approved
0.6602	Remote Similarity	NPD7146	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5695	Phase 3
0.6574	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6051	Approved
0.6569	Remote Similarity	NPD3133	Approved
0.6569	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4786	Approved
0.6569	Remote Similarity	NPD3665	Phase 1
0.6569	Remote Similarity	NPD3666	Approved
0.6566	Remote Similarity	NPD7645	Phase 2
0.656	Remote Similarity	NPD8293	Discontinued
0.6555	Remote Similarity	NPD6274	Approved
0.6542	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD4269	Approved
0.6535	Remote Similarity	NPD4270	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6505	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4695	Discontinued
0.65	Remote Similarity	NPD7525	Registered
0.65	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4700	Approved
0.6481	Remote Similarity	NPD5282	Discontinued
0.6476	Remote Similarity	NPD6672	Approved
0.6476	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5737	Approved
0.6476	Remote Similarity	NPD6903	Approved
0.6471	Remote Similarity	NPD7154	Phase 3
0.6466	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6449	Remote Similarity	NPD5693	Phase 1
0.6442	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6933	Approved
0.6429	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD8074	Phase 3
0.6423	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5983	Phase 2
0.6422	Remote Similarity	NPD5210	Approved
0.6422	Remote Similarity	NPD4629	Approved
0.6417	Remote Similarity	NPD6868	Approved
0.6415	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD6929	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6387	Remote Similarity	NPD8133	Approved
0.6381	Remote Similarity	NPD7750	Discontinued
0.6364	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1696	Phase 3
0.6337	Remote Similarity	NPD6930	Phase 2
0.6337	Remote Similarity	NPD4252	Approved
0.6337	Remote Similarity	NPD4822	Approved
0.6337	Remote Similarity	NPD4820	Approved
0.6337	Remote Similarity	NPD4821	Approved
0.6337	Remote Similarity	NPD6931	Approved
0.6337	Remote Similarity	NPD4819	Approved
0.633	Remote Similarity	NPD6001	Approved
0.6327	Remote Similarity	NPD6942	Approved
0.6327	Remote Similarity	NPD7339	Approved
0.6327	Remote Similarity	NPD8264	Approved
0.632	Remote Similarity	NPD7604	Phase 2

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