NPASS Compound

Structure

CID138139 OpenBabel06191715492D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 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:	316.2
Volume:	344.632
LogP:	4.248
LogD:	4.215
LogS:	-4.526
# Rotatable Bonds:	4
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.788
Synthetic Accessibility Score:	4.051
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175
MDCK Permeability:	1.8292610548087396e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	92.34793090820312%
Volume Distribution (VD):	1.187
Pgp-substrate:	3.048100471496582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.261
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.406
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	3.796
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.106
Carcinogencity:	0.763
Eye Corrosion:	0.179
Eye Irritation:	0.463
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC138139

Natural Product ID:	NPC138139
*Common Name:**	Lambertiainc Acid
IUPAC Name:	(1S,4aR,5S,8aR)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:	Lambertiainc Acid; Lambertianic Acid
Standard InCHIKey:	ZQHJXKYYELWEOK-CUDHKJQZSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14-5-8-17-19(2,10-4-11-20(17,3)18(21)22)16(14)7-6-15-9-12-23-13-15/h9,12-13,16-17H,1,4-8,10-11H2,2-3H3,(H,21,22)/t16-,17+,19+,20-/m0/s1
SMILES:	C=C1CC[C@@H]2[C@](C)(CCC[C@]2(C)C(=O)O)[C@H]1CCc1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463690
PubChem CID:	11869599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12116880]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[12116880]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO2819	Angelica sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2819	Angelica sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO38	Brickellia glomerata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5629	Trimusculus reticulatus	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6592	Viguiera gilliesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4696	Sisymbrium irio	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2819	Angelica sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3781	Prorocentrum minimum	Species	Prorocentraceae	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
IC50	1
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	130200.0	nM	PMID[512238]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	92.8	%	PMID[512240]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	100.2	%	PMID[512240]

☑ 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 NPC138139 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	221
0.1-0.2	1246
0.2-0.3	2446
0.3-0.4	6232
0.4-0.5	12539
0.5-0.6	11398
0.6-0.7	7584
0.7-0.8	797
0.8-0.85	147
0.85-0.9	67
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46536
0.9746	High Similarity	NPC16922
0.9669	High Similarity	NPC207294
0.9669	High Similarity	NPC112706
0.9593	High Similarity	NPC89133
0.9587	High Similarity	NPC83178
0.9583	High Similarity	NPC179354
0.9504	High Similarity	NPC74612
0.9344	High Similarity	NPC23086
0.9339	High Similarity	NPC130275
0.918	High Similarity	NPC243269
0.9174	High Similarity	NPC477967
0.9076	High Similarity	NPC208906
0.9076	High Similarity	NPC144745
0.9068	High Similarity	NPC150895
0.904	High Similarity	NPC477040
0.9016	High Similarity	NPC36255
0.9008	High Similarity	NPC202260
0.8976	High Similarity	NPC61788
0.8968	High Similarity	NPC223063
0.8968	High Similarity	NPC120836
0.8943	High Similarity	NPC272899
0.8898	High Similarity	NPC476925
0.8889	High Similarity	NPC327527
0.8889	High Similarity	NPC476917
0.8889	High Similarity	NPC477966
0.8889	High Similarity	NPC477123
0.8871	High Similarity	NPC83115
0.8864	High Similarity	NPC90953
0.8846	High Similarity	NPC476947
0.8843	High Similarity	NPC243704
0.8837	High Similarity	NPC218838
0.8828	High Similarity	NPC298190
0.8806	High Similarity	NPC121158
0.88	High Similarity	NPC230979
0.88	High Similarity	NPC303010
0.8779	High Similarity	NPC46896
0.876	High Similarity	NPC212918
0.8741	High Similarity	NPC267632
0.874	High Similarity	NPC477039
0.872	High Similarity	NPC477038
0.872	High Similarity	NPC477965
0.8712	High Similarity	NPC42400
0.8712	High Similarity	NPC307401
0.871	High Similarity	NPC317217
0.8702	High Similarity	NPC158525
0.8676	High Similarity	NPC251865
0.8676	High Similarity	NPC476944
0.8661	High Similarity	NPC246392
0.8661	High Similarity	NPC290955
0.8657	High Similarity	NPC148374
0.8647	High Similarity	NPC476943
0.8636	High Similarity	NPC146872
0.8626	High Similarity	NPC471998
0.8615	High Similarity	NPC471817
0.8594	High Similarity	NPC26532
0.8571	High Similarity	NPC310830
0.8561	High Similarity	NPC92941
0.855	High Similarity	NPC470740
0.8527	High Similarity	NPC198904
0.8527	High Similarity	NPC208389
0.8519	High Similarity	NPC56197
0.8519	High Similarity	NPC67003
0.8516	High Similarity	NPC476016
0.8504	High Similarity	NPC474829
0.8504	High Similarity	NPC290193
0.8504	High Similarity	NPC300098
0.85	High Similarity	NPC1811
0.85	High Similarity	NPC26157
0.8489	Intermediate Similarity	NPC471174
0.8489	Intermediate Similarity	NPC255414
0.8489	Intermediate Similarity	NPC216755
0.8473	Intermediate Similarity	NPC473982
0.8456	Intermediate Similarity	NPC205765
0.845	Intermediate Similarity	NPC474438
0.845	Intermediate Similarity	NPC279877
0.845	Intermediate Similarity	NPC329707
0.845	Intermediate Similarity	NPC474279
0.8438	Intermediate Similarity	NPC329922
0.8438	Intermediate Similarity	NPC474260
0.8438	Intermediate Similarity	NPC329694
0.8438	Intermediate Similarity	NPC81912
0.8433	Intermediate Similarity	NPC215109
0.8433	Intermediate Similarity	NPC470742
0.8433	Intermediate Similarity	NPC170604
0.8425	Intermediate Similarity	NPC188377
0.8425	Intermediate Similarity	NPC65735
0.8425	Intermediate Similarity	NPC118853
0.8417	Intermediate Similarity	NPC346
0.8417	Intermediate Similarity	NPC105249
0.8409	Intermediate Similarity	NPC471006
0.8394	Intermediate Similarity	NPC52412
0.8394	Intermediate Similarity	NPC263337
0.8385	Intermediate Similarity	NPC59502
0.8372	Intermediate Similarity	NPC474830
0.8372	Intermediate Similarity	NPC319140
0.8372	Intermediate Similarity	NPC95567
0.837	Intermediate Similarity	NPC236532
0.837	Intermediate Similarity	NPC220094
0.8369	Intermediate Similarity	NPC234494
0.8369	Intermediate Similarity	NPC195325
0.8369	Intermediate Similarity	NPC125182
0.8369	Intermediate Similarity	NPC69647
0.8369	Intermediate Similarity	NPC472654
0.8359	Intermediate Similarity	NPC71274
0.8359	Intermediate Similarity	NPC473885
0.8359	Intermediate Similarity	NPC471559
0.8359	Intermediate Similarity	NPC471074
0.8359	Intermediate Similarity	NPC75557
0.8357	Intermediate Similarity	NPC250228
0.8357	Intermediate Similarity	NPC476937
0.8357	Intermediate Similarity	NPC476938
0.8333	Intermediate Similarity	NPC243577
0.8333	Intermediate Similarity	NPC471995
0.8333	Intermediate Similarity	NPC97566
0.8333	Intermediate Similarity	NPC476946
0.8321	Intermediate Similarity	NPC20500
0.832	Intermediate Similarity	NPC473969
0.8319	Intermediate Similarity	NPC471521
0.8319	Intermediate Similarity	NPC473356
0.831	Intermediate Similarity	NPC228842
0.831	Intermediate Similarity	NPC470997
0.831	Intermediate Similarity	NPC212257
0.8298	Intermediate Similarity	NPC476942
0.8298	Intermediate Similarity	NPC93666
0.8298	Intermediate Similarity	NPC476941
0.8273	Intermediate Similarity	NPC199044
0.8273	Intermediate Similarity	NPC142113
0.8273	Intermediate Similarity	NPC238843
0.8271	Intermediate Similarity	NPC474425
0.8271	Intermediate Similarity	NPC474407
0.8271	Intermediate Similarity	NPC474426
0.8271	Intermediate Similarity	NPC293253
0.8264	Intermediate Similarity	NPC277525
0.8252	Intermediate Similarity	NPC272590
0.825	Intermediate Similarity	NPC177331
0.8248	Intermediate Similarity	NPC90296
0.824	Intermediate Similarity	NPC87466
0.8214	Intermediate Similarity	NPC185456
0.8214	Intermediate Similarity	NPC5676
0.8203	Intermediate Similarity	NPC475818
0.8203	Intermediate Similarity	NPC476351
0.8201	Intermediate Similarity	NPC223415
0.8194	Intermediate Similarity	NPC469503
0.8194	Intermediate Similarity	NPC268905
0.8194	Intermediate Similarity	NPC121615
0.8194	Intermediate Similarity	NPC75906
0.8194	Intermediate Similarity	NPC246164
0.8194	Intermediate Similarity	NPC472672
0.8194	Intermediate Similarity	NPC294511
0.8194	Intermediate Similarity	NPC33938
0.8162	Intermediate Similarity	NPC186626
0.816	Intermediate Similarity	NPC131801
0.8156	Intermediate Similarity	NPC262198
0.8156	Intermediate Similarity	NPC471292
0.8145	Intermediate Similarity	NPC28054
0.814	Intermediate Similarity	NPC178382
0.8138	Intermediate Similarity	NPC282445
0.8138	Intermediate Similarity	NPC178932
0.8138	Intermediate Similarity	NPC98206
0.8138	Intermediate Similarity	NPC237259
0.8138	Intermediate Similarity	NPC302054
0.8138	Intermediate Similarity	NPC30222
0.8138	Intermediate Similarity	NPC34421
0.8138	Intermediate Similarity	NPC253201
0.8125	Intermediate Similarity	NPC289911
0.8125	Intermediate Similarity	NPC473379
0.8125	Intermediate Similarity	NPC471549
0.8125	Intermediate Similarity	NPC283284
0.811	Intermediate Similarity	NPC474817
0.8102	Intermediate Similarity	NPC472376
0.8099	Intermediate Similarity	NPC302987
0.8099	Intermediate Similarity	NPC221809
0.8099	Intermediate Similarity	NPC71821
0.8095	Intermediate Similarity	NPC187547
0.8095	Intermediate Similarity	NPC21831
0.8092	Intermediate Similarity	NPC471554
0.8092	Intermediate Similarity	NPC473355
0.8092	Intermediate Similarity	NPC471573
0.8092	Intermediate Similarity	NPC471501
0.8088	Intermediate Similarity	NPC214572
0.8085	Intermediate Similarity	NPC56731
0.8085	Intermediate Similarity	NPC290038
0.8082	Intermediate Similarity	NPC35000
0.8082	Intermediate Similarity	NPC155939
0.8082	Intermediate Similarity	NPC141538
0.8082	Intermediate Similarity	NPC92979
0.8082	Intermediate Similarity	NPC281258
0.8082	Intermediate Similarity	NPC469336
0.8082	Intermediate Similarity	NPC296807
0.8071	Intermediate Similarity	NPC470741
0.8069	Intermediate Similarity	NPC476940
0.8069	Intermediate Similarity	NPC476939
0.8047	Intermediate Similarity	NPC79557
0.8047	Intermediate Similarity	NPC474136
0.8045	Intermediate Similarity	NPC21460
0.8042	Intermediate Similarity	NPC471007
0.8029	Intermediate Similarity	NPC4764
0.8029	Intermediate Similarity	NPC310043
0.8028	Intermediate Similarity	NPC276676

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 NPC138139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	891
0.2-0.3	1586
0.3-0.4	2624
0.4-0.5	2283
0.5-0.6	1236
0.6-0.7	294
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8309	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6273	Approved
0.7718	Intermediate Similarity	NPD5760	Phase 2
0.7718	Intermediate Similarity	NPD5761	Phase 2
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7003	Approved
0.7481	Intermediate Similarity	NPD2797	Approved
0.7388	Intermediate Similarity	NPD1608	Approved
0.7348	Intermediate Similarity	NPD5585	Approved
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7319	Intermediate Similarity	NPD6832	Phase 2
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6355	Discontinued
0.7299	Intermediate Similarity	NPD2798	Approved
0.7292	Intermediate Similarity	NPD2346	Discontinued
0.7292	Intermediate Similarity	NPD2344	Approved
0.7286	Intermediate Similarity	NPD8032	Phase 2
0.7279	Intermediate Similarity	NPD1876	Approved
0.7279	Intermediate Similarity	NPD1283	Approved
0.7266	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3972	Approved
0.7234	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD4476	Approved
0.7222	Intermediate Similarity	NPD6765	Approved
0.7222	Intermediate Similarity	NPD6764	Approved
0.7222	Intermediate Similarity	NPD4477	Approved
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD17	Approved
0.7154	Intermediate Similarity	NPD1241	Discontinued
0.7153	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9717	Approved
0.7108	Intermediate Similarity	NPD8434	Phase 2
0.7105	Intermediate Similarity	NPD7458	Discontinued
0.7103	Intermediate Similarity	NPD1551	Phase 2
0.7103	Intermediate Similarity	NPD2935	Discontinued
0.7101	Intermediate Similarity	NPD1203	Approved
0.7097	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2309	Approved
0.7092	Intermediate Similarity	NPD3764	Approved
0.708	Intermediate Similarity	NPD4359	Approved
0.7059	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1281	Approved
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7048	Intermediate Similarity	NPD6785	Approved
0.7048	Intermediate Similarity	NPD6784	Approved
0.7047	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1778	Approved
0.7032	Intermediate Similarity	NPD7819	Suspended
0.7027	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3750	Approved
0.7007	Intermediate Similarity	NPD4534	Discontinued
0.6993	Remote Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD2979	Phase 3
0.6978	Remote Similarity	NPD3266	Approved
0.6978	Remote Similarity	NPD3267	Approved
0.6974	Remote Similarity	NPD920	Approved
0.6972	Remote Similarity	NPD6798	Discontinued
0.697	Remote Similarity	NPD5951	Approved
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6599	Discontinued
0.6944	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6004	Phase 3
0.6939	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6005	Phase 3
0.6939	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3748	Approved
0.6901	Remote Similarity	NPD7008	Discontinued
0.6901	Remote Similarity	NPD7095	Approved
0.6899	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2182	Approved
0.6892	Remote Similarity	NPD5958	Discontinued
0.6889	Remote Similarity	NPD9545	Approved
0.6883	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD8127	Discontinued
0.6875	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD3134	Approved
0.6861	Remote Similarity	NPD3496	Discontinued
0.6853	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1243	Approved
0.6838	Remote Similarity	NPD5691	Approved
0.6835	Remote Similarity	NPD7768	Phase 2
0.6831	Remote Similarity	NPD2614	Approved
0.6828	Remote Similarity	NPD4618	Approved
0.6828	Remote Similarity	NPD4622	Approved
0.6821	Remote Similarity	NPD7440	Discontinued
0.6815	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5647	Approved
0.6809	Remote Similarity	NPD1019	Discontinued
0.6809	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6663	Approved
0.6806	Remote Similarity	NPD4870	Approved
0.6806	Remote Similarity	NPD6233	Phase 2
0.6806	Remote Similarity	NPD4062	Phase 3
0.68	Remote Similarity	NPD1238	Approved
0.68	Remote Similarity	NPD8166	Discontinued
0.6795	Remote Similarity	NPD7411	Suspended
0.6792	Remote Similarity	NPD3749	Approved
0.6788	Remote Similarity	NPD4626	Approved
0.6776	Remote Similarity	NPD6799	Approved
0.6763	Remote Similarity	NPD1481	Phase 2
0.6761	Remote Similarity	NPD5736	Approved
0.6757	Remote Similarity	NPD2438	Suspended
0.6757	Remote Similarity	NPD2796	Approved
0.6757	Remote Similarity	NPD2531	Phase 2
0.6755	Remote Similarity	NPD3887	Approved
0.6755	Remote Similarity	NPD2354	Approved
0.6753	Remote Similarity	NPD7427	Discontinued
0.675	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD9493	Approved
0.6739	Remote Similarity	NPD3847	Discontinued
0.6738	Remote Similarity	NPD6362	Approved
0.6738	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD411	Approved
0.6735	Remote Similarity	NPD5689	Approved
0.6735	Remote Similarity	NPD5688	Approved
0.6716	Remote Similarity	NPD2629	Approved
0.6715	Remote Similarity	NPD1651	Approved
0.6714	Remote Similarity	NPD5327	Phase 3
0.6712	Remote Similarity	NPD1933	Approved
0.6712	Remote Similarity	NPD447	Suspended
0.6711	Remote Similarity	NPD5762	Approved
0.6711	Remote Similarity	NPD5763	Approved
0.6707	Remote Similarity	NPD6559	Discontinued
0.6692	Remote Similarity	NPD5535	Approved
0.6691	Remote Similarity	NPD1535	Discovery
0.6689	Remote Similarity	NPD7033	Discontinued
0.6688	Remote Similarity	NPD5049	Phase 3
0.6687	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7157	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2897	Discontinued
0.6667	Remote Similarity	NPD6653	Approved
0.6646	Remote Similarity	NPD6279	Approved
0.6646	Remote Similarity	NPD6280	Approved
0.6646	Remote Similarity	NPD919	Approved
0.6645	Remote Similarity	NPD3869	Phase 3
0.6645	Remote Similarity	NPD3873	Phase 3
0.6644	Remote Similarity	NPD3140	Approved
0.6644	Remote Similarity	NPD6100	Approved
0.6644	Remote Similarity	NPD3142	Approved
0.6644	Remote Similarity	NPD6099	Approved
0.6643	Remote Similarity	NPD9494	Approved
0.6641	Remote Similarity	NPD1930	Approved
0.6641	Remote Similarity	NPD1929	Approved
0.6641	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6808	Phase 2
0.6624	Remote Similarity	NPD7028	Phase 2
0.6623	Remote Similarity	NPD2532	Approved
0.6623	Remote Similarity	NPD2534	Approved
0.6623	Remote Similarity	NPD2533	Approved
0.6623	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7097	Phase 1
0.6601	Remote Similarity	NPD7236	Approved
0.66	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2353	Approved
0.6599	Remote Similarity	NPD5735	Approved
0.6589	Remote Similarity	NPD164	Approved
0.6589	Remote Similarity	NPD5909	Discontinued
0.6582	Remote Similarity	NPD6677	Suspended
0.6582	Remote Similarity	NPD6873	Phase 2
0.6579	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6287	Discontinued
0.6566	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7177	Discontinued
0.6565	Remote Similarity	NPD1358	Approved
0.6562	Remote Similarity	NPD2296	Approved
0.6562	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2651	Approved
0.6561	Remote Similarity	NPD2649	Approved
0.6556	Remote Similarity	NPD1549	Phase 2
0.6554	Remote Similarity	NPD6353	Approved
0.6549	Remote Similarity	NPD3225	Approved
0.6547	Remote Similarity	NPD3019	Approved
0.6547	Remote Similarity	NPD2932	Approved
0.6545	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6801	Discontinued
0.6541	Remote Similarity	NPD7577	Discontinued
0.6538	Remote Similarity	NPD9697	Approved
0.6538	Remote Similarity	NPD5403	Approved
0.6531	Remote Similarity	NPD1240	Approved
0.6528	Remote Similarity	NPD454	Approved
0.6527	Remote Similarity	NPD5844	Phase 1
0.6516	Remote Similarity	NPD5401	Approved
0.6516	Remote Similarity	NPD4662	Approved
0.6516	Remote Similarity	NPD4661	Approved
0.6515	Remote Similarity	NPD2684	Approved
0.6513	Remote Similarity	NPD2800	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