NPASS Compound

Structure

NPC471412 OpenBabel07101718182D 24 26 0 0 1 0 0 0 0 0999 V2000 0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3154 3.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7969 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5412 -0.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2197 -0.5392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8603 0.4985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0273 -0.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4714 0.0668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.8889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8165 0.9658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.8519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2920 1.7734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1257 -0.9547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7781 0.9154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 20 1 1 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 18 1 0 0 0 0 16 21 1 6 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 19 20 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	358.695
LogP:	3.495
LogD:	3.304
LogS:	-3.777
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	4.448
Fsp3:	0.8
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:	-4.73
MDCK Permeability:	2.1607012968161143e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.296
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.112

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	94.75231170654297%
Volume Distribution (VD):	1.573
Pgp-substrate:	6.073434829711914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.479
CYP2C9-inhibitor:	0.366
CYP2C9-substrate:	0.769
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	13.246
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.379
Carcinogencity:	0.537
Eye Corrosion:	0.008
Eye Irritation:	0.075
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC471412

Natural Product ID:	NPC471412
*Common Name:**	(Rel 3S,5S,8R,9R,10S)-3,9-Dihydroxy-13(14)-Labden-16,15-Olide
IUPAC Name:	4-[2-[(1R,2R,4aS,6S,8aS)-1,6-dihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	ATTIPSBEQLOBCO-FUCXWFLUSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-13-5-6-15-18(2,3)16(21)8-10-19(15,4)20(13,23)11-7-14-9-12-24-17(14)22/h9,13,15-16,21,23H,5-8,10-12H2,1-4H3/t13-,15+,16+,19+,20-/m1/s1
SMILES:	O=C1OCC=C1CC[C@@]1(O)[C@H](C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436610
PubChem CID:	51040815
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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[463067]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[463067]

☑ 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 NPC471412 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	201
0.1-0.2	1173
0.2-0.3	3834
0.3-0.4	6862
0.4-0.5	13502
0.5-0.6	6890
0.6-0.7	6407
0.7-0.8	3429
0.8-0.85	321
0.85-0.9	64
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC471413
0.9684	High Similarity	NPC162973
0.957	High Similarity	NPC29952
0.9158	High Similarity	NPC234993
0.9158	High Similarity	NPC134072
0.9082	High Similarity	NPC476081
0.9043	High Similarity	NPC139692
0.901	High Similarity	NPC275539
0.901	High Similarity	NPC189075
0.899	High Similarity	NPC120321
0.8947	High Similarity	NPC105490
0.8911	High Similarity	NPC110496
0.8889	High Similarity	NPC476769
0.8878	High Similarity	NPC476767
0.8878	High Similarity	NPC117685
0.8878	High Similarity	NPC471041
0.8842	High Similarity	NPC7349
0.8812	High Similarity	NPC34768
0.88	High Similarity	NPC112009
0.8774	High Similarity	NPC471816
0.8763	High Similarity	NPC242848
0.8725	High Similarity	NPC187435
0.8725	High Similarity	NPC179380
0.8725	High Similarity	NPC67321
0.8725	High Similarity	NPC302788
0.8723	High Similarity	NPC174342
0.87	High Similarity	NPC475038
0.87	High Similarity	NPC109195
0.8687	High Similarity	NPC201406
0.8687	High Similarity	NPC47024
0.8687	High Similarity	NPC251680
0.8673	High Similarity	NPC474343
0.8667	High Similarity	NPC470063
0.8667	High Similarity	NPC12046
0.8667	High Similarity	NPC277769
0.8667	High Similarity	NPC4573
0.8667	High Similarity	NPC90952
0.8667	High Similarity	NPC194951
0.866	High Similarity	NPC276110
0.8654	High Similarity	NPC179642
0.8641	High Similarity	NPC306265
0.8641	High Similarity	NPC89171
0.8641	High Similarity	NPC476802
0.8627	High Similarity	NPC469607
0.8614	High Similarity	NPC180204
0.8614	High Similarity	NPC254202
0.8614	High Similarity	NPC478057
0.8598	High Similarity	NPC72772
0.8598	High Similarity	NPC196931
0.8598	High Similarity	NPC469794
0.8586	High Similarity	NPC108368
0.8586	High Similarity	NPC57079
0.8586	High Similarity	NPC23364
0.8585	High Similarity	NPC25909
0.8585	High Similarity	NPC157441
0.8571	High Similarity	NPC202833
0.8557	High Similarity	NPC250075
0.8557	High Similarity	NPC57117
0.8542	High Similarity	NPC472975
0.8526	High Similarity	NPC5509
0.8515	High Similarity	NPC165250
0.8515	High Similarity	NPC295791
0.85	High Similarity	NPC476299
0.85	High Similarity	NPC306856
0.85	High Similarity	NPC474012
0.85	High Similarity	NPC470074
0.85	High Similarity	NPC54705
0.85	High Similarity	NPC324841
0.8495	Intermediate Similarity	NPC65661
0.8495	Intermediate Similarity	NPC86316
0.8495	Intermediate Similarity	NPC106416
0.8491	Intermediate Similarity	NPC269530
0.8485	Intermediate Similarity	NPC51499
0.8485	Intermediate Similarity	NPC84335
0.8485	Intermediate Similarity	NPC38530
0.8485	Intermediate Similarity	NPC253826
0.8469	Intermediate Similarity	NPC183012
0.8454	Intermediate Similarity	NPC472871
0.8447	Intermediate Similarity	NPC127609
0.8447	Intermediate Similarity	NPC478208
0.8438	Intermediate Similarity	NPC51486
0.8438	Intermediate Similarity	NPC78973
0.8438	Intermediate Similarity	NPC232202
0.8431	Intermediate Similarity	NPC95899
0.8431	Intermediate Similarity	NPC282233
0.8431	Intermediate Similarity	NPC36688
0.8431	Intermediate Similarity	NPC95585
0.8421	Intermediate Similarity	NPC104560
0.8416	Intermediate Similarity	NPC247701
0.8416	Intermediate Similarity	NPC222875
0.8416	Intermediate Similarity	NPC268829
0.8416	Intermediate Similarity	NPC295110
0.8416	Intermediate Similarity	NPC25177
0.8416	Intermediate Similarity	NPC303559
0.8416	Intermediate Similarity	NPC11974
0.8404	Intermediate Similarity	NPC131813
0.84	Intermediate Similarity	NPC107806
0.84	Intermediate Similarity	NPC325229
0.84	Intermediate Similarity	NPC316598
0.84	Intermediate Similarity	NPC216478
0.84	Intermediate Similarity	NPC275086
0.84	Intermediate Similarity	NPC72647
0.84	Intermediate Similarity	NPC218107
0.84	Intermediate Similarity	NPC278673
0.8396	Intermediate Similarity	NPC469656
0.8396	Intermediate Similarity	NPC469655
0.8396	Intermediate Similarity	NPC474846
0.8387	Intermediate Similarity	NPC32223
0.8384	Intermediate Similarity	NPC209297
0.8384	Intermediate Similarity	NPC475380
0.8384	Intermediate Similarity	NPC471039
0.8381	Intermediate Similarity	NPC476759
0.8381	Intermediate Similarity	NPC474243
0.8365	Intermediate Similarity	NPC475294
0.8364	Intermediate Similarity	NPC469380
0.8351	Intermediate Similarity	NPC472814
0.8351	Intermediate Similarity	NPC473944
0.8351	Intermediate Similarity	NPC177037
0.8351	Intermediate Similarity	NPC72845
0.835	Intermediate Similarity	NPC118911
0.8349	Intermediate Similarity	NPC134430
0.8349	Intermediate Similarity	NPC473968
0.8349	Intermediate Similarity	NPC475809
0.8349	Intermediate Similarity	NPC284068
0.8333	Intermediate Similarity	NPC470953
0.8333	Intermediate Similarity	NPC31058
0.8333	Intermediate Similarity	NPC114540
0.8333	Intermediate Similarity	NPC155332
0.8333	Intermediate Similarity	NPC116620
0.8333	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC32577
0.8333	Intermediate Similarity	NPC469606
0.8333	Intermediate Similarity	NPC273005
0.8318	Intermediate Similarity	NPC476801
0.8317	Intermediate Similarity	NPC472972
0.8317	Intermediate Similarity	NPC476274
0.8317	Intermediate Similarity	NPC38855
0.8302	Intermediate Similarity	NPC472666
0.8302	Intermediate Similarity	NPC5103
0.83	Intermediate Similarity	NPC175351
0.83	Intermediate Similarity	NPC121402
0.83	Intermediate Similarity	NPC132753
0.83	Intermediate Similarity	NPC285513
0.83	Intermediate Similarity	NPC473963
0.83	Intermediate Similarity	NPC151681
0.83	Intermediate Similarity	NPC224356
0.83	Intermediate Similarity	NPC311241
0.83	Intermediate Similarity	NPC254496
0.83	Intermediate Similarity	NPC475446
0.83	Intermediate Similarity	NPC100912
0.8288	Intermediate Similarity	NPC476962
0.8286	Intermediate Similarity	NPC476479
0.8286	Intermediate Similarity	NPC476765
0.8283	Intermediate Similarity	NPC259042
0.8283	Intermediate Similarity	NPC279974
0.8283	Intermediate Similarity	NPC90014
0.8283	Intermediate Similarity	NPC266899
0.8283	Intermediate Similarity	NPC157686
0.8269	Intermediate Similarity	NPC478052
0.8269	Intermediate Similarity	NPC266570
0.8265	Intermediate Similarity	NPC472303
0.8265	Intermediate Similarity	NPC475657
0.8265	Intermediate Similarity	NPC162615
0.8265	Intermediate Similarity	NPC205034
0.8265	Intermediate Similarity	NPC152778
0.8265	Intermediate Similarity	NPC115021
0.8252	Intermediate Similarity	NPC196471
0.8252	Intermediate Similarity	NPC160583
0.8252	Intermediate Similarity	NPC45897
0.8252	Intermediate Similarity	NPC189588
0.8252	Intermediate Similarity	NPC187302
0.8252	Intermediate Similarity	NPC471938
0.8252	Intermediate Similarity	NPC97487
0.8252	Intermediate Similarity	NPC476237
0.8252	Intermediate Similarity	NPC471208
0.8252	Intermediate Similarity	NPC10232
0.8247	Intermediate Similarity	NPC158488
0.8247	Intermediate Similarity	NPC310479
0.8241	Intermediate Similarity	NPC469496
0.8241	Intermediate Similarity	NPC962
0.8241	Intermediate Similarity	NPC469463
0.8241	Intermediate Similarity	NPC469454
0.8235	Intermediate Similarity	NPC476223
0.8235	Intermediate Similarity	NPC475958
0.8235	Intermediate Similarity	NPC476240
0.8235	Intermediate Similarity	NPC224720
0.8235	Intermediate Similarity	NPC81530
0.8235	Intermediate Similarity	NPC475099
0.8229	Intermediate Similarity	NPC106332
0.8229	Intermediate Similarity	NPC50847
0.8218	Intermediate Similarity	NPC478056
0.8218	Intermediate Similarity	NPC476806
0.8218	Intermediate Similarity	NPC119036
0.8218	Intermediate Similarity	NPC114274
0.8218	Intermediate Similarity	NPC476807
0.8211	Intermediate Similarity	NPC73038
0.8211	Intermediate Similarity	NPC471219
0.8208	Intermediate Similarity	NPC112457
0.8208	Intermediate Similarity	NPC322912
0.8208	Intermediate Similarity	NPC478210

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 NPC471412 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1465
0.2-0.3	3522
0.3-0.4	2430
0.4-0.5	1018
0.5-0.6	258
0.6-0.7	177
0.7-0.8	105
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8776	High Similarity	NPD7638	Approved
0.8687	High Similarity	NPD7640	Approved
0.8687	High Similarity	NPD7639	Approved
0.8172	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6686	Approved
0.8037	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD7632	Discontinued
0.7944	Intermediate Similarity	NPD6899	Approved
0.7944	Intermediate Similarity	NPD6881	Approved
0.7931	Intermediate Similarity	NPD7507	Approved
0.7925	Intermediate Similarity	NPD5739	Approved
0.7925	Intermediate Similarity	NPD7128	Approved
0.7925	Intermediate Similarity	NPD6675	Approved
0.7925	Intermediate Similarity	NPD6402	Approved
0.7864	Intermediate Similarity	NPD4225	Approved
0.785	Intermediate Similarity	NPD5697	Approved
0.7822	Intermediate Similarity	NPD7748	Approved
0.78	Intermediate Similarity	NPD7515	Phase 2
0.78	Intermediate Similarity	NPD6079	Approved
0.7798	Intermediate Similarity	NPD7290	Approved
0.7798	Intermediate Similarity	NPD6883	Approved
0.7798	Intermediate Similarity	NPD7102	Approved
0.7798	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD6011	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7748	Intermediate Similarity	NPD4632	Approved
0.7731	Intermediate Similarity	NPD7319	Approved
0.7727	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD8130	Phase 1
0.7727	Intermediate Similarity	NPD6649	Approved
0.7727	Intermediate Similarity	NPD6847	Approved
0.7727	Intermediate Similarity	NPD6617	Approved
0.7727	Intermediate Similarity	NPD6650	Approved
0.7706	Intermediate Similarity	NPD6373	Approved
0.7706	Intermediate Similarity	NPD6372	Approved
0.7706	Intermediate Similarity	NPD6012	Approved
0.7706	Intermediate Similarity	NPD6013	Approved
0.7706	Intermediate Similarity	NPD6014	Approved
0.7699	Intermediate Similarity	NPD7115	Discovery
0.7685	Intermediate Similarity	NPD5701	Approved
0.7658	Intermediate Similarity	NPD8297	Approved
0.7658	Intermediate Similarity	NPD6882	Approved
0.7596	Intermediate Similarity	NPD7902	Approved
0.7593	Intermediate Similarity	NPD6008	Approved
0.7576	Intermediate Similarity	NPD3573	Approved
0.7568	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1694	Approved
0.7544	Intermediate Similarity	NPD6009	Approved
0.7523	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7475	Intermediate Similarity	NPD3618	Phase 1
0.7458	Intermediate Similarity	NPD7604	Phase 2
0.7455	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7436	Intermediate Similarity	NPD5983	Phase 2
0.7429	Intermediate Similarity	NPD6083	Phase 2
0.7429	Intermediate Similarity	NPD5173	Approved
0.7429	Intermediate Similarity	NPD6084	Phase 2
0.7429	Intermediate Similarity	NPD4755	Approved
0.7395	Intermediate Similarity	NPD7492	Approved
0.7383	Intermediate Similarity	NPD5223	Approved
0.7379	Intermediate Similarity	NPD5779	Approved
0.7379	Intermediate Similarity	NPD6399	Phase 3
0.7379	Intermediate Similarity	NPD5778	Approved
0.735	Intermediate Similarity	NPD6054	Approved
0.7339	Intermediate Similarity	NPD5141	Approved
0.7333	Intermediate Similarity	NPD4697	Phase 3
0.7333	Intermediate Similarity	NPD6336	Discontinued
0.7333	Intermediate Similarity	NPD6616	Approved
0.7328	Intermediate Similarity	NPD7327	Approved
0.7328	Intermediate Similarity	NPD6335	Approved
0.7328	Intermediate Similarity	NPD7328	Approved
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7308	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7900	Approved
0.7304	Intermediate Similarity	NPD6868	Approved
0.7304	Intermediate Similarity	NPD6274	Approved
0.73	Intermediate Similarity	NPD6684	Approved
0.73	Intermediate Similarity	NPD7334	Approved
0.73	Intermediate Similarity	NPD7146	Approved
0.73	Intermediate Similarity	NPD7521	Approved
0.73	Intermediate Similarity	NPD6409	Approved
0.73	Intermediate Similarity	NPD5330	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.7273	Intermediate Similarity	NPD7078	Approved
0.7265	Intermediate Similarity	NPD7101	Approved
0.7265	Intermediate Similarity	NPD7100	Approved
0.7265	Intermediate Similarity	NPD7516	Approved
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7241	Intermediate Similarity	NPD6317	Approved
0.7227	Intermediate Similarity	NPD6370	Approved
0.7222	Intermediate Similarity	NPD5344	Discontinued
0.7213	Intermediate Similarity	NPD7736	Approved
0.7212	Intermediate Similarity	NPD4202	Approved
0.7203	Intermediate Similarity	NPD8294	Approved
0.7203	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD8377	Approved
0.72	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6698	Approved
0.7184	Intermediate Similarity	NPD46	Approved
0.7179	Intermediate Similarity	NPD6314	Approved
0.7179	Intermediate Similarity	NPD6313	Approved
0.7168	Intermediate Similarity	NPD4634	Approved
0.7157	Intermediate Similarity	NPD6903	Approved
0.7157	Intermediate Similarity	NPD5737	Approved
0.7157	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD8380	Approved
0.7143	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD8379	Approved
0.7143	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD8296	Approved
0.7143	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD8033	Approved
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.7115	Intermediate Similarity	NPD5693	Phase 1
0.7115	Intermediate Similarity	NPD8035	Phase 2
0.7115	Intermediate Similarity	NPD8034	Phase 2
0.7115	Intermediate Similarity	NPD6411	Approved
0.71	Intermediate Similarity	NPD3665	Phase 1
0.71	Intermediate Similarity	NPD3133	Approved
0.71	Intermediate Similarity	NPD3666	Approved
0.71	Intermediate Similarity	NPD4786	Approved
0.7091	Intermediate Similarity	NPD4754	Approved
0.7083	Intermediate Similarity	NPD5988	Approved
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3667	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7037	Intermediate Similarity	NPD5696	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD5785	Approved
0.7018	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD6909	Approved
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.6983	Remote Similarity	NPD8133	Approved
0.6972	Remote Similarity	NPD6648	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6961	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7637	Suspended
0.6923	Remote Similarity	NPD6080	Approved
0.6923	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD6051	Approved
0.6923	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD6673	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5135	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5169	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5247	Approved
0.6869	Remote Similarity	NPD7525	Registered
0.6842	Remote Similarity	NPD5168	Approved
0.6837	Remote Similarity	NPD6114	Approved
0.6837	Remote Similarity	NPD6115	Approved
0.6837	Remote Similarity	NPD6697	Approved
0.6837	Remote Similarity	NPD6118	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.681	Remote Similarity	NPD5127	Approved
0.68	Remote Similarity	NPD6033	Approved
0.6796	Remote Similarity	NPD4519	Discontinued
0.6796	Remote Similarity	NPD4623	Approved
0.6783	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7260	Phase 2
0.6765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5210	Approved
0.6759	Remote Similarity	NPD4629	Approved
0.6754	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4221	Approved
0.6733	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD6921	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