NPASS Compound

Structure

NPC127609 OpenBabel07101719132D 28 31 0 0 1 0 0 0 0 0999 V2000 -0.7700 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7812 -0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7812 -0.9430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7812 -2.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 1 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 21 1 6 0 0 0 16 24 1 1 0 0 0 17 21 1 6 0 0 0 17 22 1 0 0 0 0 18 23 1 1 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 20 28 1 0 0 0 0 21 5 1 6 0 0 0 22 6 1 6 0 0 0 23 13 1 6 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.26
Volume:	410.817
LogP:	3.449
LogD:	2.856
LogS:	-3.914
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	5.002
Fsp3:	0.87
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092
MDCK Permeability:	3.4993030567420647e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.137
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.248
Plasma Protein Binding (PPB):	83.93682098388672%
Volume Distribution (VD):	0.888
Pgp-substrate:	10.755266189575195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.493
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	2.38
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.168
Carcinogencity:	0.233
Eye Corrosion:	0.017
Eye Irritation:	0.653
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC127609

Natural Product ID:	NPC127609
*Common Name:**	Aquilarabietic Acid C
IUPAC Name:	(4R,4aR,6R,7aR,10aS,11aR,11bR)-6-hydroxy-4,9,9,11b-tetramethyl-7a-propan-2-yl-2,3,4a,5,6,10a,11,11a-octahydro-1H-naphtho[1,2-f][1,3]benzodioxole-4-carboxylic acid
Synonyms:	Aquilarabietic acid C
Standard InCHIKey:	XVQABXWHRIIOBL-SHCWEXKVSA-N
Standard InCHI:	InChI=1S/C23H36O5/c1-13(2)23-12-14-15(10-18(23)27-20(3,4)28-23)21(5)8-7-9-22(6,19(25)26)17(21)11-16(14)24/h12-13,15-18,24H,7-11H2,1-6H3,(H,25,26)/t15-,16+,17+,18-,21+,22+,23-/m0/s1
SMILES:	CC(C)[C@@]12C=C3[C@H](C[C@@H]1OC(C)(C)O2)[C@@]1(C)CCC[C@](C)([C@@H]1C[C@H]3O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333391
PubChem CID:	71578568
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO33033	chinese eaglewood	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23394318]

☑ 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	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1072	Individual Protein	Serotonin transporter	Rattus norvegicus	Inhibition	=	54.9	%	PMID[479479]
NPT2	Others	Unspecified		Inhibition	=	37.6	%	PMID[479479]

☑ 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 NPC127609 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	195
0.1-0.2	1175
0.2-0.3	3693
0.3-0.4	6903
0.4-0.5	13205
0.5-0.6	6871
0.6-0.7	6357
0.7-0.8	4044
0.8-0.85	234
0.85-0.9	19
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8776	High Similarity	NPC470957
0.8776	High Similarity	NPC470958
0.8762	High Similarity	NPC472534
0.8762	High Similarity	NPC143706
0.8727	High Similarity	NPC122971
0.8716	High Similarity	NPC473968
0.8704	High Similarity	NPC181145
0.8624	High Similarity	NPC259306
0.8624	High Similarity	NPC470628
0.8624	High Similarity	NPC474046
0.8611	High Similarity	NPC311592
0.8611	High Similarity	NPC75167
0.8611	High Similarity	NPC157441
0.8586	High Similarity	NPC250075
0.8571	High Similarity	NPC230541
0.8544	High Similarity	NPC476769
0.8532	High Similarity	NPC470919
0.8532	High Similarity	NPC469877
0.8529	High Similarity	NPC476767
0.8519	High Similarity	NPC302146
0.8519	High Similarity	NPC194951
0.8519	High Similarity	NPC269530
0.8519	High Similarity	NPC174836
0.8519	High Similarity	NPC12046
0.8505	High Similarity	NPC83005
0.8491	Intermediate Similarity	NPC275539
0.8491	Intermediate Similarity	NPC189075
0.8462	Intermediate Similarity	NPC36688
0.8447	Intermediate Similarity	NPC471412
0.844	Intermediate Similarity	NPC474410
0.844	Intermediate Similarity	NPC293658
0.8411	Intermediate Similarity	NPC141350
0.8396	Intermediate Similarity	NPC110496
0.8393	Intermediate Similarity	NPC475775
0.8393	Intermediate Similarity	NPC476529
0.8381	Intermediate Similarity	NPC222161
0.8381	Intermediate Similarity	NPC258532
0.8378	Intermediate Similarity	NPC473590
0.8367	Intermediate Similarity	NPC477917
0.8364	Intermediate Similarity	NPC472274
0.835	Intermediate Similarity	NPC471413
0.8348	Intermediate Similarity	NPC470922
0.8333	Intermediate Similarity	NPC254496
0.8333	Intermediate Similarity	NPC474343
0.8333	Intermediate Similarity	NPC472214
0.8333	Intermediate Similarity	NPC473231
0.8333	Intermediate Similarity	NPC472215
0.8333	Intermediate Similarity	NPC478211
0.8319	Intermediate Similarity	NPC109607
0.8319	Intermediate Similarity	NPC107338
0.8319	Intermediate Similarity	NPC48692
0.8317	Intermediate Similarity	NPC266899
0.8302	Intermediate Similarity	NPC469607
0.8302	Intermediate Similarity	NPC252296
0.8288	Intermediate Similarity	NPC471816
0.8288	Intermediate Similarity	NPC474734
0.8283	Intermediate Similarity	NPC232202
0.8273	Intermediate Similarity	NPC51978
0.8273	Intermediate Similarity	NPC25909
0.8257	Intermediate Similarity	NPC469656
0.8257	Intermediate Similarity	NPC473921
0.8257	Intermediate Similarity	NPC132790
0.8257	Intermediate Similarity	NPC247031
0.8257	Intermediate Similarity	NPC100329
0.8257	Intermediate Similarity	NPC475668
0.8257	Intermediate Similarity	NPC474846
0.8257	Intermediate Similarity	NPC475480
0.8257	Intermediate Similarity	NPC469655
0.8257	Intermediate Similarity	NPC97939
0.8252	Intermediate Similarity	NPC23364
0.8246	Intermediate Similarity	NPC473250
0.8241	Intermediate Similarity	NPC112457
0.8241	Intermediate Similarity	NPC5475
0.8241	Intermediate Similarity	NPC173905
0.8241	Intermediate Similarity	NPC472216
0.8241	Intermediate Similarity	NPC284828
0.823	Intermediate Similarity	NPC477071
0.823	Intermediate Similarity	NPC475041
0.8224	Intermediate Similarity	NPC184512
0.8224	Intermediate Similarity	NPC187435
0.8224	Intermediate Similarity	NPC293512
0.8224	Intermediate Similarity	NPC67321
0.8224	Intermediate Similarity	NPC301666
0.8214	Intermediate Similarity	NPC469684
0.8214	Intermediate Similarity	NPC13713
0.8208	Intermediate Similarity	NPC471293
0.8205	Intermediate Similarity	NPC42399
0.8205	Intermediate Similarity	NPC470780
0.82	Intermediate Similarity	NPC475972
0.8198	Intermediate Similarity	NPC117712
0.8198	Intermediate Similarity	NPC474181
0.819	Intermediate Similarity	NPC238397
0.819	Intermediate Similarity	NPC469606
0.819	Intermediate Similarity	NPC31058
0.819	Intermediate Similarity	NPC471363
0.819	Intermediate Similarity	NPC273005
0.819	Intermediate Similarity	NPC162973
0.819	Intermediate Similarity	NPC137430
0.819	Intermediate Similarity	NPC295791
0.8182	Intermediate Similarity	NPC246028
0.8182	Intermediate Similarity	NPC472002
0.8173	Intermediate Similarity	NPC472644
0.8173	Intermediate Similarity	NPC20113
0.8173	Intermediate Similarity	NPC161527
0.8173	Intermediate Similarity	NPC228251
0.8173	Intermediate Similarity	NPC477972
0.8173	Intermediate Similarity	NPC219285
0.8173	Intermediate Similarity	NPC477971
0.8173	Intermediate Similarity	NPC477968
0.8165	Intermediate Similarity	NPC101450
0.8165	Intermediate Similarity	NPC475134
0.8165	Intermediate Similarity	NPC475563
0.8165	Intermediate Similarity	NPC119550
0.8165	Intermediate Similarity	NPC5103
0.8155	Intermediate Similarity	NPC285513
0.8148	Intermediate Similarity	NPC472218
0.8148	Intermediate Similarity	NPC392
0.8148	Intermediate Similarity	NPC48548
0.8148	Intermediate Similarity	NPC219900
0.8148	Intermediate Similarity	NPC177524
0.8148	Intermediate Similarity	NPC306265
0.8148	Intermediate Similarity	NPC128795
0.8148	Intermediate Similarity	NPC217921
0.8148	Intermediate Similarity	NPC472217
0.8148	Intermediate Similarity	NPC472219
0.8148	Intermediate Similarity	NPC135015
0.8137	Intermediate Similarity	NPC134067
0.8131	Intermediate Similarity	NPC478208
0.8131	Intermediate Similarity	NPC102352
0.8125	Intermediate Similarity	NPC152199
0.8125	Intermediate Similarity	NPC179626
0.8125	Intermediate Similarity	NPC134869
0.8125	Intermediate Similarity	NPC235539
0.8113	Intermediate Similarity	NPC8196
0.8113	Intermediate Similarity	NPC254202
0.8113	Intermediate Similarity	NPC69171
0.8113	Intermediate Similarity	NPC475889
0.8113	Intermediate Similarity	NPC99266
0.8113	Intermediate Similarity	NPC474165
0.8113	Intermediate Similarity	NPC7644
0.8113	Intermediate Similarity	NPC127933
0.8113	Intermediate Similarity	NPC471208
0.8113	Intermediate Similarity	NPC474775
0.8113	Intermediate Similarity	NPC134270
0.8113	Intermediate Similarity	NPC7613
0.8108	Intermediate Similarity	NPC469463
0.8108	Intermediate Similarity	NPC475966
0.8108	Intermediate Similarity	NPC469454
0.8108	Intermediate Similarity	NPC469496
0.8108	Intermediate Similarity	NPC264153
0.8103	Intermediate Similarity	NPC67251
0.81	Intermediate Similarity	NPC158488
0.81	Intermediate Similarity	NPC476004
0.81	Intermediate Similarity	NPC474761
0.8095	Intermediate Similarity	NPC472643
0.8095	Intermediate Similarity	NPC303559
0.8091	Intermediate Similarity	NPC201992
0.8091	Intermediate Similarity	NPC188738
0.8091	Intermediate Similarity	NPC324683
0.8073	Intermediate Similarity	NPC316974
0.8073	Intermediate Similarity	NPC40728
0.8073	Intermediate Similarity	NPC476759
0.8073	Intermediate Similarity	NPC206618
0.8073	Intermediate Similarity	NPC478210
0.807	Intermediate Similarity	NPC474179
0.807	Intermediate Similarity	NPC475834
0.8061	Intermediate Similarity	NPC329692
0.8058	Intermediate Similarity	NPC234993
0.8058	Intermediate Similarity	NPC134072
0.8058	Intermediate Similarity	NPC29952
0.8056	Intermediate Similarity	NPC144854
0.8056	Intermediate Similarity	NPC3316
0.8056	Intermediate Similarity	NPC475176
0.8056	Intermediate Similarity	NPC125423
0.8056	Intermediate Similarity	NPC59530
0.8056	Intermediate Similarity	NPC88013
0.8053	Intermediate Similarity	NPC284068
0.8053	Intermediate Similarity	NPC470775
0.8053	Intermediate Similarity	NPC23046
0.8053	Intermediate Similarity	NPC176513
0.8051	Intermediate Similarity	NPC298841
0.8039	Intermediate Similarity	NPC57117
0.8037	Intermediate Similarity	NPC264867
0.8037	Intermediate Similarity	NPC470321
0.8037	Intermediate Similarity	NPC473207
0.8037	Intermediate Similarity	NPC81567
0.8037	Intermediate Similarity	NPC201880
0.8037	Intermediate Similarity	NPC473543
0.8036	Intermediate Similarity	NPC474906
0.8036	Intermediate Similarity	NPC18547
0.8034	Intermediate Similarity	NPC8369
0.8034	Intermediate Similarity	NPC318135
0.802	Intermediate Similarity	NPC477574
0.802	Intermediate Similarity	NPC234335
0.802	Intermediate Similarity	NPC141831
0.8019	Intermediate Similarity	NPC476081
0.8019	Intermediate Similarity	NPC136289
0.8019	Intermediate Similarity	NPC58329
0.8019	Intermediate Similarity	NPC183571
0.8018	Intermediate Similarity	NPC222834

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 NPC127609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1368
0.2-0.3	3540
0.3-0.4	2543
0.4-0.5	942
0.5-0.6	267
0.6-0.7	225
0.7-0.8	102
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD6686	Approved
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.7905	Intermediate Similarity	NPD7638	Approved
0.7815	Intermediate Similarity	NPD7507	Approved
0.7736	Intermediate Similarity	NPD4225	Approved
0.7627	Intermediate Similarity	NPD8513	Phase 3
0.7627	Intermediate Similarity	NPD8517	Approved
0.7627	Intermediate Similarity	NPD8516	Approved
0.7627	Intermediate Similarity	NPD8515	Approved
0.7623	Intermediate Similarity	NPD7319	Approved
0.7596	Intermediate Similarity	NPD5779	Approved
0.7596	Intermediate Similarity	NPD5778	Approved
0.7589	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7115	Discovery
0.7586	Intermediate Similarity	NPD6009	Approved
0.7583	Intermediate Similarity	NPD7492	Approved
0.7542	Intermediate Similarity	NPD6054	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7521	Intermediate Similarity	NPD6616	Approved
0.7478	Intermediate Similarity	NPD8133	Approved
0.7459	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD8293	Discontinued
0.7456	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6399	Phase 3
0.7417	Intermediate Similarity	NPD6370	Approved
0.7411	Intermediate Similarity	NPD6412	Phase 2
0.7398	Intermediate Similarity	NPD7736	Approved
0.7391	Intermediate Similarity	NPD6882	Approved
0.7368	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7632	Discontinued
0.7345	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD6016	Approved
0.7333	Intermediate Similarity	NPD6411	Approved
0.7328	Intermediate Similarity	NPD4632	Approved
0.7321	Intermediate Similarity	NPD6402	Approved
0.7321	Intermediate Similarity	NPD7128	Approved
0.7321	Intermediate Similarity	NPD5739	Approved
0.7321	Intermediate Similarity	NPD6008	Approved
0.7321	Intermediate Similarity	NPD6675	Approved
0.7317	Intermediate Similarity	NPD8074	Phase 3
0.7288	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5988	Approved
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.7241	Intermediate Similarity	NPD8297	Approved
0.7227	Intermediate Similarity	NPD7327	Approved
0.7227	Intermediate Similarity	NPD7328	Approved
0.7213	Intermediate Similarity	NPD8328	Phase 3
0.7196	Intermediate Similarity	NPD7748	Approved
0.7193	Intermediate Similarity	NPD6899	Approved
0.7193	Intermediate Similarity	NPD6881	Approved
0.7193	Intermediate Similarity	NPD7320	Approved
0.719	Intermediate Similarity	NPD8033	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.7167	Intermediate Similarity	NPD7516	Approved
0.7157	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.7129	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3667	Approved
0.712	Intermediate Similarity	NPD6033	Approved
0.7107	Intermediate Similarity	NPD8377	Approved
0.7107	Intermediate Similarity	NPD6319	Approved
0.7107	Intermediate Similarity	NPD8294	Approved
0.7105	Intermediate Similarity	NPD5697	Approved
0.7105	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5701	Approved
0.7091	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD46	Approved
0.7075	Intermediate Similarity	NPD6698	Approved
0.7073	Intermediate Similarity	NPD7604	Phase 2
0.7069	Intermediate Similarity	NPD7102	Approved
0.7069	Intermediate Similarity	NPD7290	Approved
0.7069	Intermediate Similarity	NPD6883	Approved
0.7049	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD8296	Approved
0.7049	Intermediate Similarity	NPD8380	Approved
0.7049	Intermediate Similarity	NPD8335	Approved
0.7049	Intermediate Similarity	NPD7503	Approved
0.7049	Intermediate Similarity	NPD8378	Approved
0.7049	Intermediate Similarity	NPD8379	Approved
0.7043	Intermediate Similarity	NPD6011	Approved
0.7009	Intermediate Similarity	NPD7983	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6079	Approved
0.7009	Intermediate Similarity	NPD7637	Suspended
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6983	Remote Similarity	NPD6012	Approved
0.6983	Remote Similarity	NPD6013	Approved
0.6983	Remote Similarity	NPD6014	Approved
0.6964	Remote Similarity	NPD5344	Discontinued
0.696	Remote Similarity	NPD6336	Discontinued
0.6935	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD6371	Approved
0.6903	Remote Similarity	NPD5211	Phase 2
0.6857	Remote Similarity	NPD7334	Approved
0.6857	Remote Similarity	NPD6409	Approved
0.6857	Remote Similarity	NPD5330	Approved
0.6857	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD7146	Approved
0.6857	Remote Similarity	NPD3618	Phase 1
0.6857	Remote Similarity	NPD7521	Approved
0.6847	Remote Similarity	NPD4755	Approved
0.6827	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6051	Approved
0.6792	Remote Similarity	NPD3573	Approved
0.6792	Remote Similarity	NPD7524	Approved
0.6783	Remote Similarity	NPD5141	Approved
0.6762	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD1694	Approved
0.6762	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5222	Approved
0.6757	Remote Similarity	NPD5221	Approved
0.6757	Remote Similarity	NPD7839	Suspended
0.6757	Remote Similarity	NPD4697	Phase 3
0.6731	Remote Similarity	NPD6695	Phase 3
0.6729	Remote Similarity	NPD6903	Approved
0.6729	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5737	Approved
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4700	Approved
0.6726	Remote Similarity	NPD5286	Approved
0.6726	Remote Similarity	NPD4696	Approved
0.6726	Remote Similarity	NPD6648	Approved
0.6726	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD8035	Phase 2
0.6697	Remote Similarity	NPD8034	Phase 2
0.6697	Remote Similarity	NPD5693	Phase 1
0.6696	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3665	Phase 1
0.664	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD4634	Approved
0.6639	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD5696	Approved
0.6636	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4202	Approved
0.6613	Remote Similarity	NPD7100	Approved
0.6613	Remote Similarity	NPD7101	Approved
0.6609	Remote Similarity	NPD5225	Approved
0.6609	Remote Similarity	NPD5224	Approved
0.6609	Remote Similarity	NPD5226	Approved
0.6609	Remote Similarity	NPD4633	Approved
0.6606	Remote Similarity	NPD5785	Approved
0.6585	Remote Similarity	NPD6317	Approved
0.6571	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD7154	Phase 3
0.6569	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7260	Phase 2
0.6552	Remote Similarity	NPD5174	Approved
0.6552	Remote Similarity	NPD5175	Approved
0.6552	Remote Similarity	NPD4754	Approved
0.6542	Remote Similarity	NPD6098	Approved
0.6542	Remote Similarity	NPD4519	Discontinued
0.6542	Remote Similarity	NPD4623	Approved
0.6542	Remote Similarity	NPD5786	Approved
0.6532	Remote Similarity	NPD6314	Approved
0.6532	Remote Similarity	NPD6313	Approved
0.6514	Remote Similarity	NPD6080	Approved
0.6514	Remote Similarity	NPD4753	Phase 2
0.6514	Remote Similarity	NPD6904	Approved
0.6514	Remote Similarity	NPD6673	Approved
0.6508	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6908	Approved
0.6508	Remote Similarity	NPD6909	Approved
0.6481	Remote Similarity	NPD7750	Discontinued
0.6481	Remote Similarity	NPD4250	Approved
0.6481	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD7838	Discovery
0.6442	Remote Similarity	NPD4695	Discontinued
0.6442	Remote Similarity	NPD6930	Phase 2
0.6442	Remote Similarity	NPD6931	Approved
0.6442	Remote Similarity	NPD7525	Registered
0.6441	Remote Similarity	NPD4768	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