NPASS Compound

Structure

CID16967 OpenBabel06191715342D 27 29 0 0 1 0 0 0 0 0999 V2000 0.6810 2.5886 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 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 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 0.0933 1.7796 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 0.5000 0.8660 0.0000 C 0 0 0 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 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 1 0 0 0 18 27 1 0 0 0 0 19 22 1 1 0 0 0 19 23 1 0 0 0 0 20 23 1 1 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 4 1 1 0 0 0 23 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.23
Volume:	402.673
LogP:	3.928
LogD:	3.759
LogS:	-4.377
# Rotatable Bonds:	4
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	4.877
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.893
MDCK Permeability:	2.473188033036422e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.763
30% Bioavailability (F30%):	0.246

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	85.35318756103516%
Volume Distribution (VD):	1.157
Pgp-substrate:	13.851961135864258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.47
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.354
CYP2C9-substrate:	0.434
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.617
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	8.74
Half-life (T1/2):	0.457

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.527
Carcinogencity:	0.042
Eye Corrosion:	0.005
Eye Irritation:	0.169
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC16967

Natural Product ID:	NPC16967
*Common Name:**	14-Deoxy-11,12-Didehydro-15-Isopropylideneandrographolide
IUPAC Name:	3-[(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]-5-propan-2-ylidenefuran-2-one
Synonyms:
Standard InCHIKey:	NOBUCQWGEOIPGK-ZCDHJCLFSA-N
Standard InCHI:	InChI=1S/C23H32O4/c1-14(2)18-12-16(21(26)27-18)7-8-17-15(3)6-9-19-22(17,4)11-10-20(25)23(19,5)13-24/h7-8,12,17,19-20,24-25H,3,6,9-11,13H2,1-2,4-5H3/b8-7+/t17-,19+,20-,22+,23+/m1/s1
SMILES:	OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2/C=C/C1=CC(=C(C)C)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205812
PubChem CID:	637300
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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT497	Individual Protein	Maltase-glucoamylase	Homo sapiens	Inhibition	=	17.1	%	PMID[476735]
NPT497	Individual Protein	Maltase-glucoamylase	Homo sapiens	Inhibition	=	17.1	%	PMID[476736]

☑ 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 NPC16967 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	972
0.2-0.3	3319
0.3-0.4	6222
0.4-0.5	15434
0.5-0.6	8690
0.6-0.7	6240
0.7-0.8	1451
0.8-0.85	136
0.85-0.9	39
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC191521
0.9663	High Similarity	NPC162615
0.9663	High Similarity	NPC152778
0.9663	High Similarity	NPC205034
0.9438	High Similarity	NPC310479
0.9222	High Similarity	NPC182136
0.9149	High Similarity	NPC474440
0.914	High Similarity	NPC473153
0.9011	High Similarity	NPC78973
0.9011	High Similarity	NPC280149
0.9011	High Similarity	NPC221111
0.8989	High Similarity	NPC131813
0.8947	High Similarity	NPC278673
0.8913	High Similarity	NPC72845
0.8817	High Similarity	NPC139692
0.8788	High Similarity	NPC266570
0.8723	High Similarity	NPC470255
0.8673	High Similarity	NPC155332
0.8673	High Similarity	NPC114540
0.8673	High Similarity	NPC32577
0.8646	High Similarity	NPC73911
0.8632	High Similarity	NPC276110
0.8617	High Similarity	NPC53555
0.8617	High Similarity	NPC472812
0.86	High Similarity	NPC34768
0.8557	High Similarity	NPC57079
0.8557	High Similarity	NPC108368
0.8542	High Similarity	NPC234993
0.8542	High Similarity	NPC134072
0.8542	High Similarity	NPC242848
0.8529	High Similarity	NPC75389
0.8526	High Similarity	NPC57117
0.8515	High Similarity	NPC179380
0.8511	High Similarity	NPC472811
0.8495	Intermediate Similarity	NPC50488
0.8495	Intermediate Similarity	NPC474396
0.8444	Intermediate Similarity	NPC79945
0.8444	Intermediate Similarity	NPC311070
0.8438	Intermediate Similarity	NPC209355
0.8431	Intermediate Similarity	NPC275060
0.8416	Intermediate Similarity	NPC81630
0.8416	Intermediate Similarity	NPC218158
0.84	Intermediate Similarity	NPC23584
0.84	Intermediate Similarity	NPC171014
0.84	Intermediate Similarity	NPC45897
0.84	Intermediate Similarity	NPC297617
0.8384	Intermediate Similarity	NPC115899
0.8367	Intermediate Similarity	NPC124512
0.8367	Intermediate Similarity	NPC92275
0.8367	Intermediate Similarity	NPC473154
0.8367	Intermediate Similarity	NPC159763
0.8367	Intermediate Similarity	NPC278386
0.8352	Intermediate Similarity	NPC96055
0.8351	Intermediate Similarity	NPC190713
0.8333	Intermediate Similarity	NPC43063
0.8333	Intermediate Similarity	NPC79298
0.8333	Intermediate Similarity	NPC475074
0.8333	Intermediate Similarity	NPC105490
0.8333	Intermediate Similarity	NPC302788
0.8316	Intermediate Similarity	NPC329842
0.83	Intermediate Similarity	NPC475038
0.83	Intermediate Similarity	NPC109195
0.83	Intermediate Similarity	NPC11956
0.83	Intermediate Similarity	NPC476081
0.8298	Intermediate Similarity	NPC174342
0.8286	Intermediate Similarity	NPC44537
0.8283	Intermediate Similarity	NPC38855
0.8283	Intermediate Similarity	NPC474012
0.8283	Intermediate Similarity	NPC266955
0.8283	Intermediate Similarity	NPC476299
0.828	Intermediate Similarity	NPC166857
0.828	Intermediate Similarity	NPC473891
0.8265	Intermediate Similarity	NPC99726
0.8265	Intermediate Similarity	NPC141401
0.8265	Intermediate Similarity	NPC51499
0.8265	Intermediate Similarity	NPC110937
0.8261	Intermediate Similarity	NPC476602
0.8261	Intermediate Similarity	NPC474013
0.8261	Intermediate Similarity	NPC109528
0.8252	Intermediate Similarity	NPC304276
0.8252	Intermediate Similarity	NPC137462
0.8242	Intermediate Similarity	NPC42476
0.8235	Intermediate Similarity	NPC295843
0.8235	Intermediate Similarity	NPC471206
0.8235	Intermediate Similarity	NPC189863
0.8229	Intermediate Similarity	NPC7349
0.8222	Intermediate Similarity	NPC170303
0.8222	Intermediate Similarity	NPC159148
0.8218	Intermediate Similarity	NPC112009
0.8218	Intermediate Similarity	NPC120321
0.82	Intermediate Similarity	NPC168319
0.82	Intermediate Similarity	NPC194028
0.82	Intermediate Similarity	NPC303559
0.82	Intermediate Similarity	NPC471412
0.8191	Intermediate Similarity	NPC472810
0.8191	Intermediate Similarity	NPC93411
0.8191	Intermediate Similarity	NPC104560
0.8191	Intermediate Similarity	NPC472809
0.8191	Intermediate Similarity	NPC473879
0.8182	Intermediate Similarity	NPC275086
0.8182	Intermediate Similarity	NPC218107
0.8182	Intermediate Similarity	NPC325229
0.8173	Intermediate Similarity	NPC137911
0.8173	Intermediate Similarity	NPC228477
0.8173	Intermediate Similarity	NPC475065
0.8172	Intermediate Similarity	NPC329692
0.8163	Intermediate Similarity	NPC260796
0.8163	Intermediate Similarity	NPC165632
0.8163	Intermediate Similarity	NPC250757
0.8163	Intermediate Similarity	NPC301534
0.8155	Intermediate Similarity	NPC109376
0.8155	Intermediate Similarity	NPC330011
0.8155	Intermediate Similarity	NPC329048
0.8152	Intermediate Similarity	NPC302360
0.8144	Intermediate Similarity	NPC469697
0.8144	Intermediate Similarity	NPC201725
0.8132	Intermediate Similarity	NPC471218
0.8125	Intermediate Similarity	NPC472814
0.8125	Intermediate Similarity	NPC177037
0.8119	Intermediate Similarity	NPC273668
0.8111	Intermediate Similarity	NPC281880
0.8111	Intermediate Similarity	NPC268827
0.8105	Intermediate Similarity	NPC82876
0.8105	Intermediate Similarity	NPC314727
0.81	Intermediate Similarity	NPC201406
0.81	Intermediate Similarity	NPC471413
0.81	Intermediate Similarity	NPC227865
0.8095	Intermediate Similarity	NPC103491
0.8095	Intermediate Similarity	NPC16270
0.8095	Intermediate Similarity	NPC12795
0.809	Intermediate Similarity	NPC184737
0.8081	Intermediate Similarity	NPC474343
0.8081	Intermediate Similarity	NPC253826
0.8081	Intermediate Similarity	NPC2049
0.8081	Intermediate Similarity	NPC53844
0.8081	Intermediate Similarity	NPC208094
0.8077	Intermediate Similarity	NPC473482
0.8077	Intermediate Similarity	NPC475418
0.8077	Intermediate Similarity	NPC50124
0.8077	Intermediate Similarity	NPC224660
0.8077	Intermediate Similarity	NPC470024
0.8077	Intermediate Similarity	NPC318363
0.8065	Intermediate Similarity	NPC86316
0.8065	Intermediate Similarity	NPC471795
0.8065	Intermediate Similarity	NPC65661
0.8065	Intermediate Similarity	NPC30984
0.8065	Intermediate Similarity	NPC106416
0.8061	Intermediate Similarity	NPC472441
0.8061	Intermediate Similarity	NPC295347
0.8061	Intermediate Similarity	NPC183012
0.8061	Intermediate Similarity	NPC13924
0.8058	Intermediate Similarity	NPC172867
0.8058	Intermediate Similarity	NPC478208
0.8058	Intermediate Similarity	NPC478052
0.8043	Intermediate Similarity	NPC12283
0.8043	Intermediate Similarity	NPC57370
0.8043	Intermediate Similarity	NPC474193
0.8043	Intermediate Similarity	NPC474809
0.8043	Intermediate Similarity	NPC476927
0.8041	Intermediate Similarity	NPC472641
0.8041	Intermediate Similarity	NPC214697
0.8041	Intermediate Similarity	NPC38232
0.8041	Intermediate Similarity	NPC472640
0.8039	Intermediate Similarity	NPC180204
0.8039	Intermediate Similarity	NPC329345
0.8039	Intermediate Similarity	NPC473283
0.8039	Intermediate Similarity	NPC471938
0.8039	Intermediate Similarity	NPC134270
0.8039	Intermediate Similarity	NPC72151
0.8039	Intermediate Similarity	NPC475526
0.8037	Intermediate Similarity	NPC171126
0.8037	Intermediate Similarity	NPC241977
0.8022	Intermediate Similarity	NPC142163
0.8022	Intermediate Similarity	NPC475944
0.8021	Intermediate Similarity	NPC51486
0.8021	Intermediate Similarity	NPC472642
0.802	Intermediate Similarity	NPC473160
0.802	Intermediate Similarity	NPC11974
0.802	Intermediate Similarity	NPC282524
0.8019	Intermediate Similarity	NPC474315
0.8	Intermediate Similarity	NPC316598
0.8	Intermediate Similarity	NPC106332
0.8	Intermediate Similarity	NPC475068
0.8	Intermediate Similarity	NPC7280
0.8	Intermediate Similarity	NPC474629
0.8	Intermediate Similarity	NPC229612
0.7982	Intermediate Similarity	NPC185287
0.7982	Intermediate Similarity	NPC157380
0.7981	Intermediate Similarity	NPC187435
0.7981	Intermediate Similarity	NPC67321
0.7981	Intermediate Similarity	NPC473284
0.798	Intermediate Similarity	NPC475380
0.798	Intermediate Similarity	NPC471153
0.798	Intermediate Similarity	NPC162346
0.798	Intermediate Similarity	NPC209297
0.7978	Intermediate Similarity	NPC189206
0.7961	Intermediate Similarity	NPC201880
0.7961	Intermediate Similarity	NPC470321
0.7961	Intermediate Similarity	NPC81567
0.7961	Intermediate Similarity	NPC264867

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 NPC16967 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	1082
0.2-0.3	3274
0.3-0.4	2731
0.4-0.5	1350
0.5-0.6	321
0.6-0.7	219
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
0.8367	Intermediate Similarity	NPD4225	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.7921	Intermediate Similarity	NPD7640	Approved
0.7921	Intermediate Similarity	NPD7639	Approved
0.7742	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7637	Suspended
0.75	Intermediate Similarity	NPD7115	Discovery
0.7407	Intermediate Similarity	NPD6686	Approved
0.7404	Intermediate Similarity	NPD6648	Approved
0.7396	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7503	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.73	Intermediate Similarity	NPD7838	Discovery
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.7255	Intermediate Similarity	NPD7748	Approved
0.7248	Intermediate Similarity	NPD6899	Approved
0.7248	Intermediate Similarity	NPD6881	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7228	Intermediate Similarity	NPD6411	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7156	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7117	Intermediate Similarity	NPD7290	Approved
0.7117	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7102	Approved
0.7113	Intermediate Similarity	NPD6695	Phase 3
0.7064	Intermediate Similarity	NPD7128	Approved
0.7064	Intermediate Similarity	NPD5739	Approved
0.7064	Intermediate Similarity	NPD6675	Approved
0.7064	Intermediate Similarity	NPD6402	Approved
0.7059	Intermediate Similarity	NPD6079	Approved
0.7054	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD7902	Approved
0.7041	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6101	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.6991	Remote Similarity	NPD8297	Approved
0.6991	Remote Similarity	NPD6882	Approved
0.699	Remote Similarity	NPD6399	Phase 3
0.6989	Remote Similarity	NPD8264	Approved
0.6983	Remote Similarity	NPD7327	Approved
0.6983	Remote Similarity	NPD7328	Approved
0.6961	Remote Similarity	NPD5785	Approved
0.6949	Remote Similarity	NPD8033	Approved
0.6939	Remote Similarity	NPD7154	Phase 3
0.6937	Remote Similarity	NPD6011	Approved
0.6937	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD7516	Approved
0.69	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD6083	Phase 2
0.6887	Remote Similarity	NPD6084	Phase 2
0.6882	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD6924	Approved
0.6875	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6929	Approved
0.6875	Remote Similarity	NPD6373	Approved
0.6875	Remote Similarity	NPD7645	Phase 2
0.6864	Remote Similarity	NPD8294	Approved
0.6864	Remote Similarity	NPD8377	Approved
0.6863	Remote Similarity	NPD5328	Approved
0.6863	Remote Similarity	NPD6051	Approved
0.6857	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7152	Approved
0.6848	Remote Similarity	NPD7150	Approved
0.6848	Remote Similarity	NPD7151	Approved
0.6847	Remote Similarity	NPD5701	Approved
0.6837	Remote Similarity	NPD5209	Approved
0.6832	Remote Similarity	NPD7524	Approved
0.6832	Remote Similarity	NPD7750	Discontinued
0.6822	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8379	Approved
0.6807	Remote Similarity	NPD8296	Approved
0.6807	Remote Similarity	NPD8335	Approved
0.6807	Remote Similarity	NPD8380	Approved
0.6807	Remote Similarity	NPD8378	Approved
0.6804	Remote Similarity	NPD7525	Registered
0.6804	Remote Similarity	NPD6930	Phase 2
0.6804	Remote Similarity	NPD7514	Phase 3
0.6804	Remote Similarity	NPD7332	Phase 2
0.6804	Remote Similarity	NPD6931	Approved
0.6792	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5222	Approved
0.6789	Remote Similarity	NPD5211	Phase 2
0.6771	Remote Similarity	NPD7145	Approved
0.6771	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7900	Approved
0.6762	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5286	Approved
0.6759	Remote Similarity	NPD4696	Approved
0.6759	Remote Similarity	NPD5285	Approved
0.6739	Remote Similarity	NPD7144	Approved
0.6739	Remote Similarity	NPD7143	Approved
0.6737	Remote Similarity	NPD6933	Approved
0.6735	Remote Similarity	NPD6902	Approved
0.6733	Remote Similarity	NPD6409	Approved
0.6733	Remote Similarity	NPD7521	Approved
0.6733	Remote Similarity	NPD5330	Approved
0.6733	Remote Similarity	NPD6684	Approved
0.6733	Remote Similarity	NPD7334	Approved
0.6733	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD5173	Approved
0.6721	Remote Similarity	NPD7507	Approved
0.67	Remote Similarity	NPD4786	Approved
0.6699	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5225	Approved
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7509	Discontinued
0.6633	Remote Similarity	NPD4695	Discontinued
0.6632	Remote Similarity	NPD7339	Approved
0.6632	Remote Similarity	NPD8039	Approved
0.6632	Remote Similarity	NPD6942	Approved
0.663	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD6922	Approved
0.6609	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6672	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6602	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5737	Approved
0.6577	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5174	Approved
0.6574	Remote Similarity	NPD4755	Approved
0.6571	Remote Similarity	NPD8035	Phase 2
0.6571	Remote Similarity	NPD8034	Phase 2
0.6571	Remote Similarity	NPD7087	Discontinued
0.6569	Remote Similarity	NPD5279	Phase 3
0.6562	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7319	Approved
0.6555	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD3133	Approved
0.6535	Remote Similarity	NPD3665	Phase 1
0.6525	Remote Similarity	NPD6274	Approved
0.6514	Remote Similarity	NPD5696	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.6505	Remote Similarity	NPD4250	Approved
0.6505	Remote Similarity	NPD4251	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD1696	Phase 3
0.6471	Remote Similarity	NPD5363	Approved
0.6471	Remote Similarity	NPD6893	Approved
0.6465	Remote Similarity	NPD4819	Approved
0.6465	Remote Similarity	NPD4820	Approved
0.6465	Remote Similarity	NPD4821	Approved
0.6465	Remote Similarity	NPD4822	Approved
0.6455	Remote Similarity	NPD4700	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6444	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD4271	Approved
0.6429	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6313	Approved
0.6417	Remote Similarity	NPD6314	Approved
0.6415	Remote Similarity	NPD5693	Phase 1
0.6415	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD5284	Approved
0.6408	Remote Similarity	NPD4249	Approved
0.64	Remote Similarity	NPD6898	Phase 1
0.6389	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD5210	Approved
0.6389	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4753	Phase 2
0.6379	Remote Similarity	NPD6371	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD5290	Discontinued

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