NPASS Compound

Structure

NPC70320 OpenBabel07101718192D 25 27 0 0 0 0 0 0 0 0999 V2000 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -1.7321 3.0000 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 -5.1962 1.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 18 2 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 20 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 12 19 2 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	711.53
Volume:	771.402
LogP:	7.362
LogD:	4.842
LogS:	-2.861
# Rotatable Bonds:	32
TPSA:	165.78
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	4.674
Fsp3:	0.85
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.381
MDCK Permeability:	9.653789675212465e-06
Pgp-inhibitor:	0.393
Pgp-substrate:	0.29
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	96.1397933959961%
Volume Distribution (VD):	1.021
Pgp-substrate:	1.6465164422988892%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.303
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.189
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	2.276
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.278
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.96
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.113

Download Data

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

Natural Product: NPC70320

Natural Product ID:	NPC70320
*Common Name:**	Vitexdoin D
IUPAC Name:	3,7-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxynaphthalene-2-carbaldehyde
Synonyms:	vitexdoin D
Standard InCHIKey:	VEMAKQNXRTXQPD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O6/c1-24-17-6-10(3-4-14(17)21)19-12-8-16(23)18(25-2)7-11(12)5-15(22)13(19)9-20/h3-9,21-23H,1-2H3
SMILES:	COc1cc2cc(O)c(c(c2cc1O)c1ccc(c(c1)OC)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078523
PubChem CID:	44479220
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

*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	=	130.0	nM	PMID[490015]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	91.13	%	PMID[490015]

☑ 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 NPC70320 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	421
0.1-0.2	1866
0.2-0.3	4087
0.3-0.4	11402
0.4-0.5	6620
0.5-0.6	3601
0.6-0.7	6479
0.7-0.8	7137
0.8-0.85	999
0.85-0.9	74
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC137125
0.9795	High Similarity	NPC3744
0.9517	High Similarity	NPC39361
0.9379	High Similarity	NPC300603
0.9379	High Similarity	NPC91694
0.9329	High Similarity	NPC75377
0.9281	High Similarity	NPC141574
0.92	High Similarity	NPC473201
0.92	High Similarity	NPC302783
0.9097	High Similarity	NPC131905
0.9026	High Similarity	NPC143328
0.9013	High Similarity	NPC164912
0.8961	High Similarity	NPC213401
0.8961	High Similarity	NPC279605
0.8947	High Similarity	NPC118427
0.8924	High Similarity	NPC26386
0.8903	High Similarity	NPC199463
0.8903	High Similarity	NPC37543
0.8903	High Similarity	NPC178976
0.8859	High Similarity	NPC275278
0.8839	High Similarity	NPC5379
0.8839	High Similarity	NPC14561
0.8839	High Similarity	NPC77807
0.8831	High Similarity	NPC93552
0.8824	High Similarity	NPC144283
0.8824	High Similarity	NPC306011
0.8824	High Similarity	NPC472838
0.8816	High Similarity	NPC261322
0.88	High Similarity	NPC160777
0.88	High Similarity	NPC73416
0.8782	High Similarity	NPC296044
0.8782	High Similarity	NPC167098
0.8742	High Similarity	NPC477689
0.8734	High Similarity	NPC311740
0.871	High Similarity	NPC107109
0.871	High Similarity	NPC475770
0.871	High Similarity	NPC474000
0.8707	High Similarity	NPC141368
0.8701	High Similarity	NPC78505
0.8701	High Similarity	NPC256406
0.8688	High Similarity	NPC303174
0.8681	High Similarity	NPC228843
0.8675	High Similarity	NPC68441
0.8671	High Similarity	NPC84571
0.8671	High Similarity	NPC36217
0.8667	High Similarity	NPC50954
0.865	High Similarity	NPC4200
0.8649	High Similarity	NPC1268
0.8645	High Similarity	NPC149889
0.8645	High Similarity	NPC295646
0.8645	High Similarity	NPC312338
0.8636	High Similarity	NPC31132
0.8636	High Similarity	NPC58310
0.8636	High Similarity	NPC85131
0.8636	High Similarity	NPC295977
0.8634	High Similarity	NPC43319
0.863	High Similarity	NPC152209
0.8625	High Similarity	NPC101769
0.8625	High Similarity	NPC270837
0.8608	High Similarity	NPC85121
0.86	High Similarity	NPC192597
0.86	High Similarity	NPC229218
0.86	High Similarity	NPC141817
0.86	High Similarity	NPC169214
0.86	High Similarity	NPC11314
0.86	High Similarity	NPC176030
0.8591	High Similarity	NPC82336
0.8591	High Similarity	NPC78987
0.8581	High Similarity	NPC206207
0.858	High Similarity	NPC218226
0.8571	High Similarity	NPC171916
0.8571	High Similarity	NPC38545
0.8571	High Similarity	NPC329933
0.8562	High Similarity	NPC116838
0.8562	High Similarity	NPC294965
0.8562	High Similarity	NPC58373
0.8562	High Similarity	NPC34802
0.8562	High Similarity	NPC22130
0.8562	High Similarity	NPC144843
0.8562	High Similarity	NPC201800
0.8544	High Similarity	NPC136674
0.8544	High Similarity	NPC35598
0.8544	High Similarity	NPC222689
0.8543	High Similarity	NPC239608
0.8543	High Similarity	NPC46161
0.8528	High Similarity	NPC188079
0.8528	High Similarity	NPC300307
0.8526	High Similarity	NPC131121
0.8526	High Similarity	NPC474993
0.8526	High Similarity	NPC180388
0.8526	High Similarity	NPC199773
0.8516	High Similarity	NPC472279
0.8509	High Similarity	NPC236132
0.8509	High Similarity	NPC186686
0.8509	High Similarity	NPC197168
0.8506	High Similarity	NPC238279
0.8506	High Similarity	NPC139364
0.8506	High Similarity	NPC194653
0.8506	High Similarity	NPC254702
0.8506	High Similarity	NPC80710
0.8506	High Similarity	NPC166036
0.8506	High Similarity	NPC203077
0.8506	High Similarity	NPC203747
0.85	High Similarity	NPC469889
0.85	High Similarity	NPC66288
0.8491	Intermediate Similarity	NPC104876
0.8491	Intermediate Similarity	NPC245891
0.8491	Intermediate Similarity	NPC210459
0.8491	Intermediate Similarity	NPC235448
0.8491	Intermediate Similarity	NPC45846
0.8487	Intermediate Similarity	NPC196941
0.8487	Intermediate Similarity	NPC309169
0.8481	Intermediate Similarity	NPC478223
0.8481	Intermediate Similarity	NPC291878
0.8481	Intermediate Similarity	NPC195796
0.8481	Intermediate Similarity	NPC109765
0.8481	Intermediate Similarity	NPC35038
0.8481	Intermediate Similarity	NPC227062
0.8481	Intermediate Similarity	NPC278778
0.8481	Intermediate Similarity	NPC288353
0.8476	Intermediate Similarity	NPC131866
0.8471	Intermediate Similarity	NPC208806
0.8471	Intermediate Similarity	NPC62051
0.8466	Intermediate Similarity	NPC469521
0.8466	Intermediate Similarity	NPC474024
0.8466	Intermediate Similarity	NPC186392
0.8462	Intermediate Similarity	NPC474417
0.8462	Intermediate Similarity	NPC124842
0.8462	Intermediate Similarity	NPC149526
0.8457	Intermediate Similarity	NPC25361
0.8457	Intermediate Similarity	NPC293319
0.8456	Intermediate Similarity	NPC275061
0.8456	Intermediate Similarity	NPC132804
0.8456	Intermediate Similarity	NPC220344
0.8456	Intermediate Similarity	NPC243996
0.8452	Intermediate Similarity	NPC195763
0.8452	Intermediate Similarity	NPC264289
0.8452	Intermediate Similarity	NPC139293
0.8452	Intermediate Similarity	NPC333691
0.8452	Intermediate Similarity	NPC264550
0.8452	Intermediate Similarity	NPC200060
0.8452	Intermediate Similarity	NPC40290
0.8452	Intermediate Similarity	NPC142876
0.8452	Intermediate Similarity	NPC69430
0.8452	Intermediate Similarity	NPC472837
0.8447	Intermediate Similarity	NPC476247
0.8447	Intermediate Similarity	NPC469472
0.8446	Intermediate Similarity	NPC141934
0.8442	Intermediate Similarity	NPC52692
0.8438	Intermediate Similarity	NPC78944
0.8438	Intermediate Similarity	NPC228785
0.8438	Intermediate Similarity	NPC321399
0.8438	Intermediate Similarity	NPC299436
0.8438	Intermediate Similarity	NPC161947
0.8438	Intermediate Similarity	NPC56085
0.8438	Intermediate Similarity	NPC14353
0.8438	Intermediate Similarity	NPC47623
0.8438	Intermediate Similarity	NPC471973
0.8438	Intermediate Similarity	NPC474960
0.8438	Intermediate Similarity	NPC65784
0.8438	Intermediate Similarity	NPC155302
0.8431	Intermediate Similarity	NPC157133
0.8428	Intermediate Similarity	NPC27337
0.8428	Intermediate Similarity	NPC472598
0.8428	Intermediate Similarity	NPC291508
0.8428	Intermediate Similarity	NPC202495
0.8428	Intermediate Similarity	NPC472963
0.8428	Intermediate Similarity	NPC474055
0.8421	Intermediate Similarity	NPC16353
0.8421	Intermediate Similarity	NPC84266
0.8418	Intermediate Similarity	NPC226656
0.8418	Intermediate Similarity	NPC180901
0.8418	Intermediate Similarity	NPC200761
0.8418	Intermediate Similarity	NPC57674
0.8418	Intermediate Similarity	NPC67396
0.8418	Intermediate Similarity	NPC300757
0.8418	Intermediate Similarity	NPC230149
0.8418	Intermediate Similarity	NPC130589
0.8418	Intermediate Similarity	NPC477503
0.8418	Intermediate Similarity	NPC134287
0.8418	Intermediate Similarity	NPC117992
0.8418	Intermediate Similarity	NPC45849
0.8418	Intermediate Similarity	NPC168247
0.8418	Intermediate Similarity	NPC234255
0.8418	Intermediate Similarity	NPC152951
0.8418	Intermediate Similarity	NPC66508
0.8418	Intermediate Similarity	NPC470327
0.8418	Intermediate Similarity	NPC39184
0.8415	Intermediate Similarity	NPC117911
0.8411	Intermediate Similarity	NPC124365
0.8411	Intermediate Similarity	NPC84273
0.8408	Intermediate Similarity	NPC260979
0.8408	Intermediate Similarity	NPC324233
0.8408	Intermediate Similarity	NPC472912
0.8408	Intermediate Similarity	NPC471982
0.8408	Intermediate Similarity	NPC323626
0.8405	Intermediate Similarity	NPC37870
0.8405	Intermediate Similarity	NPC272502
0.84	Intermediate Similarity	NPC223336
0.84	Intermediate Similarity	NPC12668

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 NPC70320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	1015
0.2-0.3	1511
0.3-0.4	2758
0.4-0.5	1768
0.5-0.6	1033
0.6-0.7	521
0.7-0.8	127
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD6232	Discontinued
0.8675	High Similarity	NPD7422	Clinical (unspecified phase)
0.8634	High Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1934	Approved
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD2801	Approved
0.8121	Intermediate Similarity	NPD6166	Phase 2
0.8121	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8025	Intermediate Similarity	NPD3882	Suspended
0.7941	Intermediate Similarity	NPD6559	Discontinued
0.7935	Intermediate Similarity	NPD7003	Approved
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD5404	Approved
0.7908	Intermediate Similarity	NPD5406	Approved
0.7908	Intermediate Similarity	NPD5408	Approved
0.7908	Intermediate Similarity	NPD5405	Approved
0.7898	Intermediate Similarity	NPD1511	Approved
0.7875	Intermediate Similarity	NPD3226	Approved
0.7838	Intermediate Similarity	NPD9494	Approved
0.7826	Intermediate Similarity	NPD4380	Phase 2
0.7805	Intermediate Similarity	NPD7768	Phase 2
0.7805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1512	Approved
0.7793	Intermediate Similarity	NPD1201	Approved
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7785	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3817	Phase 2
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2346	Discontinued
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD1510	Phase 2
0.7719	Intermediate Similarity	NPD7074	Phase 3
0.7712	Intermediate Similarity	NPD1607	Approved
0.7711	Intermediate Similarity	NPD6234	Discontinued
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7706	Intermediate Similarity	NPD3818	Discontinued
0.7703	Intermediate Similarity	NPD1470	Approved
0.7687	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7390	Discontinued
0.7665	Intermediate Similarity	NPD5494	Approved
0.7661	Intermediate Similarity	NPD7054	Approved
0.7654	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7644	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD8313	Approved
0.7635	Intermediate Similarity	NPD1283	Approved
0.7625	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD37	Approved
0.7616	Intermediate Similarity	NPD7472	Approved
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1651	Approved
0.7582	Intermediate Similarity	NPD1240	Approved
0.758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1465	Phase 2
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1551	Phase 2
0.7561	Intermediate Similarity	NPD7411	Suspended
0.7546	Intermediate Similarity	NPD7458	Discontinued
0.7516	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4966	Approved
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7468	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD1549	Phase 2
0.7468	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3620	Phase 2
0.7451	Intermediate Similarity	NPD3764	Approved
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1281	Approved
0.7429	Intermediate Similarity	NPD7251	Discontinued
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2798	Approved
0.7415	Intermediate Similarity	NPD4626	Approved
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7412	Intermediate Similarity	NPD1247	Approved
0.741	Intermediate Similarity	NPD6801	Discontinued
0.7405	Intermediate Similarity	NPD2344	Approved
0.7399	Intermediate Similarity	NPD7177	Discontinued
0.7399	Intermediate Similarity	NPD7228	Approved
0.7386	Intermediate Similarity	NPD7808	Phase 3
0.7386	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD8166	Discontinued
0.7375	Intermediate Similarity	NPD3750	Approved
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2979	Phase 3
0.7346	Intermediate Similarity	NPD6799	Approved
0.7342	Intermediate Similarity	NPD2438	Suspended
0.7342	Intermediate Similarity	NPD2796	Approved
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3749	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3926	Phase 2
0.7308	Intermediate Similarity	NPD447	Suspended
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7257	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6273	Approved
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.723	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.7209	Intermediate Similarity	NPD8127	Discontinued
0.7208	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6674	Discontinued
0.7197	Intermediate Similarity	NPD1933	Approved
0.7188	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5283	Phase 1
0.717	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD5711	Approved
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.716	Intermediate Similarity	NPD8455	Phase 2
0.7153	Intermediate Similarity	NPD228	Approved
0.7152	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7039	Approved
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7125	Intermediate Similarity	NPD2531	Phase 2
0.7118	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5402	Approved
0.7117	Intermediate Similarity	NPD6190	Approved
0.7108	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD4908	Phase 1
0.709	Intermediate Similarity	NPD6823	Phase 2
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7028	Phase 2
0.7073	Intermediate Similarity	NPD3300	Phase 2
0.7063	Intermediate Similarity	NPD3748	Approved
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD1876	Approved
0.7055	Intermediate Similarity	NPD4110	Phase 3
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7051	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6651	Approved
0.7039	Intermediate Similarity	NPD7685	Pre-registration
0.7033	Intermediate Similarity	NPD8434	Phase 2
0.7019	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD4477	Approved
0.7019	Intermediate Similarity	NPD4476	Approved
0.7017	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7013	Intermediate Similarity	NPD1203	Approved
0.7013	Intermediate Similarity	NPD1164	Approved
0.7006	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.6994	Remote Similarity	NPD2800	Approved
0.6988	Remote Similarity	NPD5401	Approved
0.6987	Remote Similarity	NPD6832	Phase 2
0.6971	Remote Similarity	NPD7229	Phase 3
0.6971	Remote Similarity	NPD3787	Discontinued
0.697	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6962	Remote Similarity	NPD6233	Phase 2
0.6961	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4308	Phase 3
0.6954	Remote Similarity	NPD3019	Approved
0.6946	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7240	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