NPASS Compound

Structure

NPC78987 OpenBabel07101718292D 25 27 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -3.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 1 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 15 1 0 0 0 0 4 11 1 0 0 0 0 4 12 2 0 0 0 0 5 11 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 13 1 0 0 0 0 7 17 2 0 0 0 0 8 12 1 0 0 0 0 8 20 2 0 0 0 0 9 21 1 0 0 0 0 11 13 2 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 9 1 1 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	1.905
LogD:	2.092
LogS:	-3.994
# Rotatable Bonds:	4
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	2.529
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.127
MDCK Permeability:	4.786687895830255e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.921
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	93.15203857421875%
Volume Distribution (VD):	0.646
Pgp-substrate:	6.708756923675537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.708
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.38
CYP2D6-inhibitor:	0.156
CYP2D6-substrate:	0.808
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	10.53
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.794
AMES Toxicity:	0.666
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.496
Skin Sensitization:	0.948
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.375
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC78987

Natural Product ID:	NPC78987
*Common Name:**	Vitexdoin A
IUPAC Name:	(3R,4S)-6,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-3,4-dihydronaphthalene-2-carbaldehyde
Synonyms:
Standard InCHIKey:	PNRPRUVCFFHMMC-LIRRHRJNSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-25-18-6-10(2-3-15(18)22)19-13-7-17(24)16(23)5-11(13)4-12(8-20)14(19)9-21/h2-8,14,19,21-24H,9H2,1H3/t14-,19-/m0/s1
SMILES:	O=CC1=Cc2cc(O)c(cc2[C@@H]([C@H]1CO)c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079287
PubChem CID:	44478946
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	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	IC50	=	380.0	nM	PMID[540262]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	67.0	%	PMID[540262]

☑ 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 NPC78987 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	316
0.1-0.2	1434
0.2-0.3	3457
0.3-0.4	9142
0.4-0.5	9448
0.5-0.6	3562
0.6-0.7	8920
0.7-0.8	5975
0.8-0.85	312
0.85-0.9	121
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC82336
0.9149	High Similarity	NPC300603
0.9149	High Similarity	NPC91694
0.9143	High Similarity	NPC192597
0.9143	High Similarity	NPC176030
0.9143	High Similarity	NPC169214
0.9143	High Similarity	NPC229218
0.9143	High Similarity	NPC141817
0.9021	High Similarity	NPC39361
0.9	High Similarity	NPC29599
0.8905	High Similarity	NPC327410
0.8889	High Similarity	NPC304622
0.8881	High Similarity	NPC123228
0.8881	High Similarity	NPC151167
0.8881	High Similarity	NPC5018
0.8881	High Similarity	NPC123722
0.8881	High Similarity	NPC276466
0.8872	High Similarity	NPC9067
0.8849	High Similarity	NPC90431
0.8832	High Similarity	NPC239302
0.8815	High Similarity	NPC307050
0.8815	High Similarity	NPC277458
0.8806	High Similarity	NPC179777
0.8806	High Similarity	NPC84076
0.8806	High Similarity	NPC303680
0.8806	High Similarity	NPC90128
0.8777	High Similarity	NPC113295
0.8776	High Similarity	NPC475718
0.8731	High Similarity	NPC53305
0.8731	High Similarity	NPC29008
0.8731	High Similarity	NPC257589
0.8731	High Similarity	NPC266705
0.8731	High Similarity	NPC228771
0.8707	High Similarity	NPC261322
0.8705	High Similarity	NPC300776
0.8705	High Similarity	NPC4982
0.8705	High Similarity	NPC68779
0.8705	High Similarity	NPC5310
0.8705	High Similarity	NPC176814
0.8686	High Similarity	NPC311419
0.8686	High Similarity	NPC65935
0.8686	High Similarity	NPC123196
0.8686	High Similarity	NPC172673
0.8686	High Similarity	NPC137427
0.8686	High Similarity	NPC244246
0.8686	High Similarity	NPC215941
0.8686	High Similarity	NPC319282
0.8686	High Similarity	NPC275724
0.8681	High Similarity	NPC239608
0.8681	High Similarity	NPC209085
0.8681	High Similarity	NPC224884
0.8681	High Similarity	NPC46161
0.8671	High Similarity	NPC472410
0.8667	High Similarity	NPC127937
0.8667	High Similarity	NPC276014
0.8667	High Similarity	NPC92207
0.8662	High Similarity	NPC322021
0.8658	High Similarity	NPC137125
0.8658	High Similarity	NPC3744
0.8649	High Similarity	NPC475454
0.8649	High Similarity	NPC118033
0.8649	High Similarity	NPC475311
0.8649	High Similarity	NPC473579
0.8649	High Similarity	NPC473680
0.8647	High Similarity	NPC30462
0.8643	High Similarity	NPC252343
0.8643	High Similarity	NPC88065
0.8643	High Similarity	NPC95485
0.8643	High Similarity	NPC89504
0.8639	High Similarity	NPC474556
0.8609	High Similarity	NPC213401
0.86	High Similarity	NPC474000
0.8591	High Similarity	NPC144283
0.8591	High Similarity	NPC475579
0.8591	High Similarity	NPC75377
0.8591	High Similarity	NPC473773
0.8591	High Similarity	NPC70320
0.8582	High Similarity	NPC4181
0.8582	High Similarity	NPC164778
0.8582	High Similarity	NPC257976
0.8582	High Similarity	NPC242372
0.8581	High Similarity	NPC237441
0.8562	High Similarity	NPC73416
0.8562	High Similarity	NPC160777
0.854	High Similarity	NPC226661
0.8533	High Similarity	NPC164912
0.8531	High Similarity	NPC474784
0.8523	High Similarity	NPC58310
0.8523	High Similarity	NPC295977
0.8519	High Similarity	NPC273686
0.8519	High Similarity	NPC312404
0.8507	High Similarity	NPC114298
0.8507	High Similarity	NPC85488
0.8506	High Similarity	NPC131905
0.8493	Intermediate Similarity	NPC275278
0.8493	Intermediate Similarity	NPC309169
0.8493	Intermediate Similarity	NPC196941
0.8477	Intermediate Similarity	NPC475770
0.8472	Intermediate Similarity	NPC100675
0.8467	Intermediate Similarity	NPC20404
0.8467	Intermediate Similarity	NPC472838
0.8467	Intermediate Similarity	NPC293641
0.8467	Intermediate Similarity	NPC118427
0.8467	Intermediate Similarity	NPC20287
0.8467	Intermediate Similarity	NPC306011
0.8467	Intermediate Similarity	NPC12022
0.8462	Intermediate Similarity	NPC132723
0.8462	Intermediate Similarity	NPC76032
0.8456	Intermediate Similarity	NPC87113
0.8451	Intermediate Similarity	NPC120852
0.8446	Intermediate Similarity	NPC52692
0.8446	Intermediate Similarity	NPC77598
0.8446	Intermediate Similarity	NPC58373
0.8444	Intermediate Similarity	NPC229084
0.8444	Intermediate Similarity	NPC163083
0.8444	Intermediate Similarity	NPC280704
0.8444	Intermediate Similarity	NPC106659
0.8444	Intermediate Similarity	NPC18984
0.8444	Intermediate Similarity	NPC160900
0.844	Intermediate Similarity	NPC144662
0.844	Intermediate Similarity	NPC311256
0.8435	Intermediate Similarity	NPC287495
0.8435	Intermediate Similarity	NPC9370
0.8433	Intermediate Similarity	NPC201777
0.8425	Intermediate Similarity	NPC46880
0.8421	Intermediate Similarity	NPC180901
0.8421	Intermediate Similarity	NPC232316
0.8421	Intermediate Similarity	NPC95614
0.8421	Intermediate Similarity	NPC56214
0.8421	Intermediate Similarity	NPC227217
0.8421	Intermediate Similarity	NPC117780
0.8421	Intermediate Similarity	NPC165133
0.8421	Intermediate Similarity	NPC300757
0.8421	Intermediate Similarity	NPC242885
0.8417	Intermediate Similarity	NPC66905
0.8414	Intermediate Similarity	NPC52664
0.8414	Intermediate Similarity	NPC84273
0.8411	Intermediate Similarity	NPC131121
0.8406	Intermediate Similarity	NPC278308
0.8394	Intermediate Similarity	NPC120225
0.8394	Intermediate Similarity	NPC213552
0.8392	Intermediate Similarity	NPC471152
0.8389	Intermediate Similarity	NPC474903
0.838	Intermediate Similarity	NPC152209
0.837	Intermediate Similarity	NPC286573
0.8366	Intermediate Similarity	NPC279605
0.8358	Intermediate Similarity	NPC14007
0.8358	Intermediate Similarity	NPC158949
0.8358	Intermediate Similarity	NPC189844
0.8358	Intermediate Similarity	NPC207613
0.8358	Intermediate Similarity	NPC109083
0.8358	Intermediate Similarity	NPC224814
0.8358	Intermediate Similarity	NPC269843
0.8358	Intermediate Similarity	NPC60962
0.8356	Intermediate Similarity	NPC11314
0.8355	Intermediate Similarity	NPC62051
0.8355	Intermediate Similarity	NPC305710
0.8346	Intermediate Similarity	NPC310338
0.8346	Intermediate Similarity	NPC281298
0.8345	Intermediate Similarity	NPC282291
0.8345	Intermediate Similarity	NPC241354
0.8345	Intermediate Similarity	NPC166137
0.8344	Intermediate Similarity	NPC78505
0.8344	Intermediate Similarity	NPC302783
0.8344	Intermediate Similarity	NPC473201
0.8333	Intermediate Similarity	NPC203719
0.8333	Intermediate Similarity	NPC284409
0.8333	Intermediate Similarity	NPC117237
0.8321	Intermediate Similarity	NPC3221
0.8321	Intermediate Similarity	NPC148627
0.8321	Intermediate Similarity	NPC289459
0.8321	Intermediate Similarity	NPC280767
0.8311	Intermediate Similarity	NPC225351
0.831	Intermediate Similarity	NPC237594
0.831	Intermediate Similarity	NPC471942
0.831	Intermediate Similarity	NPC249791
0.831	Intermediate Similarity	NPC471110
0.831	Intermediate Similarity	NPC119060
0.831	Intermediate Similarity	NPC476387
0.8309	Intermediate Similarity	NPC31344
0.8309	Intermediate Similarity	NPC317769
0.8299	Intermediate Similarity	NPC16353
0.8299	Intermediate Similarity	NPC284881
0.8299	Intermediate Similarity	NPC474444
0.8299	Intermediate Similarity	NPC93433
0.8299	Intermediate Similarity	NPC264706
0.8299	Intermediate Similarity	NPC50954
0.8298	Intermediate Similarity	NPC227002
0.8298	Intermediate Similarity	NPC50763
0.8296	Intermediate Similarity	NPC312675
0.8296	Intermediate Similarity	NPC160380
0.8296	Intermediate Similarity	NPC473853
0.8296	Intermediate Similarity	NPC54872
0.8296	Intermediate Similarity	NPC343720
0.8296	Intermediate Similarity	NPC470212
0.8296	Intermediate Similarity	NPC324571
0.8296	Intermediate Similarity	NPC113865
0.8296	Intermediate Similarity	NPC184651
0.8296	Intermediate Similarity	NPC262156
0.8296	Intermediate Similarity	NPC38996

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 NPC78987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	928
0.2-0.3	1404
0.3-0.4	2552
0.4-0.5	2037
0.5-0.6	1080
0.6-0.7	735
0.7-0.8	118
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD9494	Approved
0.8169	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD3620	Phase 2
0.8163	Intermediate Similarity	NPD8166	Discontinued
0.7935	Intermediate Similarity	NPD37	Approved
0.7926	Intermediate Similarity	NPD5536	Phase 2
0.7911	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD5283	Phase 1
0.7857	Intermediate Similarity	NPD1283	Approved
0.7832	Intermediate Similarity	NPD3027	Phase 3
0.781	Intermediate Similarity	NPD1651	Approved
0.7806	Intermediate Similarity	NPD7028	Phase 2
0.7793	Intermediate Similarity	NPD4060	Phase 1
0.7785	Intermediate Similarity	NPD4965	Approved
0.7785	Intermediate Similarity	NPD4967	Phase 2
0.7785	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD228	Approved
0.7712	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7228	Approved
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7682	Intermediate Similarity	NPD4110	Phase 3
0.7682	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6273	Approved
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7647	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1281	Approved
0.7626	Intermediate Similarity	NPD2932	Approved
0.7622	Intermediate Similarity	NPD7473	Discontinued
0.7595	Intermediate Similarity	NPD1934	Approved
0.7594	Intermediate Similarity	NPD3022	Approved
0.7594	Intermediate Similarity	NPD3021	Approved
0.7593	Intermediate Similarity	NPD8127	Discontinued
0.7566	Intermediate Similarity	NPD7003	Approved
0.7562	Intermediate Similarity	NPD3882	Suspended
0.7551	Intermediate Similarity	NPD2979	Phase 3
0.7547	Intermediate Similarity	NPD2801	Approved
0.7547	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2438	Suspended
0.7533	Intermediate Similarity	NPD2935	Discontinued
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6190	Approved
0.7515	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD1876	Approved
0.7453	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7405	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD3818	Discontinued
0.7351	Intermediate Similarity	NPD2799	Discontinued
0.7349	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6166	Phase 2
0.7347	Intermediate Similarity	NPD7095	Approved
0.7343	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD1465	Phase 2
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4140	Approved
0.7315	Intermediate Similarity	NPD1613	Approved
0.731	Intermediate Similarity	NPD2797	Approved
0.7305	Intermediate Similarity	NPD5691	Approved
0.7303	Intermediate Similarity	NPD2531	Phase 2
0.7297	Intermediate Similarity	NPD3764	Approved
0.7294	Intermediate Similarity	NPD7685	Pre-registration
0.7284	Intermediate Similarity	NPD5978	Approved
0.7284	Intermediate Similarity	NPD5977	Approved
0.7267	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3657	Discovery
0.7267	Intermediate Similarity	NPD5735	Approved
0.726	Intermediate Similarity	NPD2798	Approved
0.7255	Intermediate Similarity	NPD7266	Discontinued
0.725	Intermediate Similarity	NPD4380	Phase 2
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7248	Intermediate Similarity	NPD8032	Phase 2
0.7248	Intermediate Similarity	NPD6663	Approved
0.7246	Intermediate Similarity	NPD1241	Discontinued
0.7226	Intermediate Similarity	NPD3750	Approved
0.7226	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5494	Approved
0.7211	Intermediate Similarity	NPD5736	Approved
0.7205	Intermediate Similarity	NPD6873	Phase 2
0.7197	Intermediate Similarity	NPD1511	Approved
0.7193	Intermediate Similarity	NPD7240	Approved
0.7192	Intermediate Similarity	NPD1470	Approved
0.7188	Intermediate Similarity	NPD3455	Phase 2
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5110	Phase 2
0.7181	Intermediate Similarity	NPD5111	Phase 2
0.7181	Intermediate Similarity	NPD3268	Approved
0.7181	Intermediate Similarity	NPD5109	Approved
0.7176	Intermediate Similarity	NPD7074	Phase 3
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6674	Discontinued
0.7161	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3092	Approved
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD4624	Approved
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7133	Intermediate Similarity	NPD4062	Phase 3
0.7132	Intermediate Similarity	NPD2684	Approved
0.7124	Intermediate Similarity	NPD1510	Phase 2
0.7118	Intermediate Similarity	NPD7054	Approved
0.7117	Intermediate Similarity	NPD7819	Suspended
0.7113	Intermediate Similarity	NPD3091	Approved
0.7107	Intermediate Similarity	NPD1512	Approved
0.7103	Intermediate Similarity	NPD1608	Approved
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6559	Discontinued
0.7089	Intermediate Similarity	NPD4357	Discontinued
0.7086	Intermediate Similarity	NPD943	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7083	Intermediate Similarity	NPD3847	Discontinued
0.7083	Intermediate Similarity	NPD3026	Approved
0.7083	Intermediate Similarity	NPD3023	Approved
0.7081	Intermediate Similarity	NPD3226	Approved
0.7078	Intermediate Similarity	NPD4476	Approved
0.7078	Intermediate Similarity	NPD4477	Approved
0.7076	Intermediate Similarity	NPD7472	Approved
0.7075	Intermediate Similarity	NPD3094	Phase 2
0.7073	Intermediate Similarity	NPD3817	Phase 2
0.707	Intermediate Similarity	NPD5241	Discontinued
0.7063	Intermediate Similarity	NPD3024	Approved
0.7063	Intermediate Similarity	NPD3025	Approved
0.7063	Intermediate Similarity	NPD1357	Approved
0.7055	Intermediate Similarity	NPD5327	Phase 3
0.7051	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7843	Approved
0.7035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3705	Approved
0.7034	Intermediate Similarity	NPD1201	Approved
0.7032	Intermediate Similarity	NPD2344	Approved
0.7027	Intermediate Similarity	NPD5647	Approved
0.7013	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8312	Approved
0.7011	Intermediate Similarity	NPD8313	Approved
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.7	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7110	Phase 1
0.6994	Remote Similarity	NPD6386	Approved
0.6994	Remote Similarity	NPD6385	Approved
0.6994	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1894	Discontinued
0.6993	Remote Similarity	NPD1607	Approved
0.6993	Remote Similarity	NPD6653	Approved
0.6988	Remote Similarity	NPD7075	Discontinued
0.6987	Remote Similarity	NPD5958	Discontinued
0.6987	Remote Similarity	NPD2424	Discontinued
0.6987	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4534	Discontinued
0.698	Remote Similarity	NPD2861	Phase 2
0.6975	Remote Similarity	NPD824	Approved
0.6975	Remote Similarity	NPD2649	Approved
0.6975	Remote Similarity	NPD2651	Approved
0.6974	Remote Similarity	NPD1240	Approved
0.6968	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD6099	Approved
0.6959	Remote Similarity	NPD3751	Discontinued
0.6957	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2313	Discontinued
0.6954	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7097	Phase 1
0.6944	Remote Similarity	NPD5585	Approved
0.6943	Remote Similarity	NPD3060	Approved
0.6941	Remote Similarity	NPD2489	Approved
0.6941	Remote Similarity	NPD2898	Approved
0.6941	Remote Similarity	NPD27	Approved
0.6937	Remote Similarity	NPD2532	Approved
0.6937	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2533	Approved
0.6937	Remote Similarity	NPD2534	Approved
0.6937	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6797	Phase 2
0.6934	Remote Similarity	NPD1358	Approved
0.6933	Remote Similarity	NPD4908	Phase 1
0.6933	Remote Similarity	NPD6875	Approved
0.6933	Remote Similarity	NPD6876	Approved
0.6928	Remote Similarity	NPD1933	Approved
0.6918	Remote Similarity	NPD1535	Discovery
0.6917	Remote Similarity	NPD3020	Approved
0.6914	Remote Similarity	NPD1653	Approved
0.6913	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6584	Phase 3
0.6909	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2674	Phase 3
0.6903	Remote Similarity	NPD4308	Phase 3

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