NPASS Compound

Structure

CID3221 OpenBabel06191715322D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.2921 -1.3255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2950 -1.9857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7216 -0.9925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7173 -2.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0010 -1.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1524 -1.3277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1128 -1.7699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1482 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 -2.3202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5744 -0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1133 -0.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1451 0.6611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5714 -0.3329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5790 -2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7185 -0.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1470 -1.9866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5778 -0.3336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5748 0.9938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0029 0.6602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1487 -1.2275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5765 1.7529 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 16 20 2 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.14
Volume:	319.426
LogP:	3.693
LogD:	3.342
LogS:	-4.586
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	4.215
Fsp3:	0.316
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:	-4.988
MDCK Permeability:	1.4503356396744493e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.784
30% Bioavailability (F30%):	0.782

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	97.89009857177734%
Volume Distribution (VD):	0.501
Pgp-substrate:	0.9888882637023926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.921
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.783
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.406

ADMET: Excretion

Clearance (CL):	11.769
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.359
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.636
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.905
Carcinogencity:	0.76
Eye Corrosion:	0.004
Eye Irritation:	0.578
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC3221

Natural Product ID:	NPC3221
*Common Name:**	Acerogenin C
IUPAC Name:	n.a.
Synonyms:	Acerogenin C
Standard InCHIKey:	DMCJCKWHLCLVNV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O3/c20-16-4-2-1-3-15-8-12-18(21)19(13-15)22-17-10-6-14(5-9-16)7-11-17/h6-8,10-13,21H,1-5,9H2
SMILES:	O=C1CCCCc2ccc(c(c2)Oc2ccc(CC1)cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL589990
PubChem CID:	10040223
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003523] Meta,para-diphenylether diarylheptanoids

*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
NPO28138	Burkea africana	Species	Fabaceae	Eukaryota	Bark	n.a.	n.a.	PMID[29394063]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20701	Leonotis leonurus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28138	Burkea africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28002	Lupinus kingii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28294	Astragalus tomentosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27547	Laminaria digitata	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28438	Dipterocarpus hasseltii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27723	Artemisia rothrockii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27767	Artemisia turcomanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28188	Rindera echinata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27898	Ormosia stipitata	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28046	Lotus hispidus	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	44.9	%	PMID[571470]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	67.8	%	PMID[571470]

☑ 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 NPC3221 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	346
0.1-0.2	1689
0.2-0.3	4767
0.3-0.4	13529
0.4-0.5	4103
0.5-0.6	4435
0.6-0.7	8873
0.7-0.8	4621
0.8-0.85	257
0.85-0.9	62
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC226661
0.9504	High Similarity	NPC53305
0.9504	High Similarity	NPC257589
0.9426	High Similarity	NPC92207
0.9426	High Similarity	NPC127937
0.9355	High Similarity	NPC241354
0.9333	High Similarity	NPC201777
0.9268	High Similarity	NPC90128
0.9268	High Similarity	NPC179777
0.9268	High Similarity	NPC303680
0.9268	High Similarity	NPC84076
0.9237	High Similarity	NPC86947
0.92	High Similarity	NPC304622
0.9194	High Similarity	NPC151167
0.9194	High Similarity	NPC276466
0.9194	High Similarity	NPC5018
0.9194	High Similarity	NPC123228
0.9194	High Similarity	NPC123722
0.918	High Similarity	NPC163083
0.9127	High Similarity	NPC244246
0.9127	High Similarity	NPC311419
0.9127	High Similarity	NPC215941
0.9127	High Similarity	NPC137427
0.9127	High Similarity	NPC123196
0.9127	High Similarity	NPC319282
0.9127	High Similarity	NPC275724
0.9127	High Similarity	NPC65935
0.9083	High Similarity	NPC299406
0.9024	High Similarity	NPC242372
0.9024	High Similarity	NPC4181
0.9024	High Similarity	NPC164778
0.9024	High Similarity	NPC257976
0.9016	High Similarity	NPC290451
0.9016	High Similarity	NPC127389
0.8952	High Similarity	NPC312404
0.8952	High Similarity	NPC273686
0.8943	High Similarity	NPC114298
0.8923	High Similarity	NPC204592
0.8889	High Similarity	NPC293641
0.8889	High Similarity	NPC12022
0.8889	High Similarity	NPC20404
0.8889	High Similarity	NPC20287
0.888	High Similarity	NPC280767
0.888	High Similarity	NPC87113
0.8846	High Similarity	NPC176814
0.8846	High Similarity	NPC4982
0.8846	High Similarity	NPC68779
0.8846	High Similarity	NPC300776
0.8846	High Similarity	NPC5310
0.8843	High Similarity	NPC470626
0.8828	High Similarity	NPC172673
0.8819	High Similarity	NPC278308
0.881	High Similarity	NPC276014
0.8806	High Similarity	NPC472332
0.8806	High Similarity	NPC472335
0.878	High Similarity	NPC158949
0.8779	High Similarity	NPC152209
0.877	High Similarity	NPC281298
0.877	High Similarity	NPC310338
0.876	High Similarity	NPC293619
0.872	High Similarity	NPC229084
0.872	High Similarity	NPC18984
0.872	High Similarity	NPC106659
0.872	High Similarity	NPC160900
0.8712	High Similarity	NPC90431
0.871	High Similarity	NPC177291
0.871	High Similarity	NPC194416
0.8702	High Similarity	NPC144662
0.8699	High Similarity	NPC165133
0.8699	High Similarity	NPC242885
0.8699	High Similarity	NPC117780
0.8699	High Similarity	NPC56214
0.8699	High Similarity	NPC227217
0.8699	High Similarity	NPC95614
0.8699	High Similarity	NPC232316
0.8692	High Similarity	NPC239302
0.8682	High Similarity	NPC66905
0.8661	High Similarity	NPC17837
0.8661	High Similarity	NPC156854
0.8661	High Similarity	NPC304630
0.8661	High Similarity	NPC134431
0.8651	High Similarity	NPC228972
0.8651	High Similarity	NPC122792
0.8636	High Similarity	NPC113295
0.8629	High Similarity	NPC60962
0.8629	High Similarity	NPC14007
0.8629	High Similarity	NPC109083
0.8629	High Similarity	NPC224814
0.8629	High Similarity	NPC189844
0.8629	High Similarity	NPC207613
0.8629	High Similarity	NPC269843
0.8626	High Similarity	NPC327410
0.8615	High Similarity	NPC469480
0.8594	High Similarity	NPC470699
0.8583	High Similarity	NPC194519
0.8582	High Similarity	NPC284409
0.8571	High Similarity	NPC317769
0.8571	High Similarity	NPC31344
0.8571	High Similarity	NPC244876
0.856	High Similarity	NPC324571
0.856	High Similarity	NPC54872
0.856	High Similarity	NPC470212
0.856	High Similarity	NPC312675
0.856	High Similarity	NPC473853
0.856	High Similarity	NPC113865
0.856	High Similarity	NPC38996
0.856	High Similarity	NPC262156
0.856	High Similarity	NPC184651
0.856	High Similarity	NPC160380
0.856	High Similarity	NPC343720
0.8538	High Similarity	NPC142985
0.8538	High Similarity	NPC195292
0.8525	High Similarity	NPC61062
0.8525	High Similarity	NPC299252
0.8525	High Similarity	NPC277394
0.8519	High Similarity	NPC474784
0.8516	High Similarity	NPC178284
0.8516	High Similarity	NPC213552
0.8516	High Similarity	NPC120225
0.8516	High Similarity	NPC191037
0.8516	High Similarity	NPC181361
0.8516	High Similarity	NPC58607
0.8504	High Similarity	NPC114901
0.8504	High Similarity	NPC48990
0.8504	High Similarity	NPC293701
0.8496	Intermediate Similarity	NPC252343
0.8492	Intermediate Similarity	NPC85488
0.8492	Intermediate Similarity	NPC286573
0.8489	Intermediate Similarity	NPC472333
0.8489	Intermediate Similarity	NPC208507
0.848	Intermediate Similarity	NPC98305
0.8462	Intermediate Similarity	NPC210655
0.8456	Intermediate Similarity	NPC29599
0.8456	Intermediate Similarity	NPC282291
0.8456	Intermediate Similarity	NPC19158
0.8456	Intermediate Similarity	NPC166137
0.8456	Intermediate Similarity	NPC100675
0.8455	Intermediate Similarity	NPC164386
0.845	Intermediate Similarity	NPC292056
0.845	Intermediate Similarity	NPC32163
0.845	Intermediate Similarity	NPC118787
0.845	Intermediate Similarity	NPC210355
0.845	Intermediate Similarity	NPC147821
0.845	Intermediate Similarity	NPC41706
0.845	Intermediate Similarity	NPC16651
0.845	Intermediate Similarity	NPC163332
0.845	Intermediate Similarity	NPC183181
0.845	Intermediate Similarity	NPC319625
0.845	Intermediate Similarity	NPC111247
0.8443	Intermediate Similarity	NPC51345
0.8438	Intermediate Similarity	NPC289459
0.8429	Intermediate Similarity	NPC116229
0.8425	Intermediate Similarity	NPC280704
0.8425	Intermediate Similarity	NPC471693
0.8421	Intermediate Similarity	NPC471110
0.8417	Intermediate Similarity	NPC257124
0.8417	Intermediate Similarity	NPC173746
0.8417	Intermediate Similarity	NPC8547
0.8417	Intermediate Similarity	NPC156840
0.8406	Intermediate Similarity	NPC160378
0.84	Intermediate Similarity	NPC265454
0.84	Intermediate Similarity	NPC34634
0.8394	Intermediate Similarity	NPC253481
0.8394	Intermediate Similarity	NPC472410
0.8394	Intermediate Similarity	NPC253722
0.8394	Intermediate Similarity	NPC31751
0.8387	Intermediate Similarity	NPC205502
0.8385	Intermediate Similarity	NPC72529
0.8382	Intermediate Similarity	NPC288452
0.8382	Intermediate Similarity	NPC289690
0.8374	Intermediate Similarity	NPC19290
0.8359	Intermediate Similarity	NPC74478
0.8359	Intermediate Similarity	NPC94276
0.8359	Intermediate Similarity	NPC109822
0.8359	Intermediate Similarity	NPC246704
0.8346	Intermediate Similarity	NPC71090
0.8346	Intermediate Similarity	NPC475468
0.8346	Intermediate Similarity	NPC41562
0.8333	Intermediate Similarity	NPC169214
0.8333	Intermediate Similarity	NPC106920
0.8333	Intermediate Similarity	NPC176030
0.8333	Intermediate Similarity	NPC273657
0.8333	Intermediate Similarity	NPC141817
0.8333	Intermediate Similarity	NPC229218
0.8333	Intermediate Similarity	NPC192597
0.8321	Intermediate Similarity	NPC326065
0.8321	Intermediate Similarity	NPC5851
0.8321	Intermediate Similarity	NPC83062
0.8321	Intermediate Similarity	NPC78987
0.8321	Intermediate Similarity	NPC82336
0.8321	Intermediate Similarity	NPC86030
0.832	Intermediate Similarity	NPC311595
0.832	Intermediate Similarity	NPC24474
0.8308	Intermediate Similarity	NPC281020
0.8308	Intermediate Similarity	NPC223807
0.8306	Intermediate Similarity	NPC280001
0.8295	Intermediate Similarity	NPC148627
0.8295	Intermediate Similarity	NPC203133
0.8295	Intermediate Similarity	NPC193544
0.8295	Intermediate Similarity	NPC475169

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 NPC3221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	994
0.2-0.3	1438
0.3-0.4	2683
0.4-0.5	1805
0.5-0.6	1091
0.6-0.7	676
0.7-0.8	122
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
0.872	High Similarity	NPD4379	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD228	Approved
0.816	Intermediate Similarity	NPD5536	Phase 2
0.813	Intermediate Similarity	NPD5283	Phase 1
0.8106	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7095	Approved
0.8045	Intermediate Similarity	NPD3027	Phase 3
0.803	Intermediate Similarity	NPD9494	Approved
0.803	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4110	Phase 3
0.7985	Intermediate Similarity	NPD6798	Discontinued
0.7984	Intermediate Similarity	NPD1535	Discovery
0.7959	Intermediate Similarity	NPD2801	Approved
0.7958	Intermediate Similarity	NPD1511	Approved
0.7953	Intermediate Similarity	NPD1894	Discontinued
0.7951	Intermediate Similarity	NPD3021	Approved
0.7951	Intermediate Similarity	NPD3022	Approved
0.7941	Intermediate Similarity	NPD6355	Discontinued
0.7923	Intermediate Similarity	NPD1608	Approved
0.7923	Intermediate Similarity	NPD1481	Phase 2
0.7891	Intermediate Similarity	NPD1651	Approved
0.7869	Intermediate Similarity	NPD2684	Approved
0.7868	Intermediate Similarity	NPD1558	Phase 1
0.7868	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD4060	Phase 1
0.7868	Intermediate Similarity	NPD1613	Approved
0.7852	Intermediate Similarity	NPD3882	Suspended
0.7847	Intermediate Similarity	NPD1512	Approved
0.7838	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD6233	Phase 2
0.7794	Intermediate Similarity	NPD4062	Phase 3
0.7744	Intermediate Similarity	NPD2797	Approved
0.7717	Intermediate Similarity	NPD6671	Approved
0.7698	Intermediate Similarity	NPD1241	Discontinued
0.7692	Intermediate Similarity	NPD17	Approved
0.7669	Intermediate Similarity	NPD1283	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD5535	Approved
0.7619	Intermediate Similarity	NPD7843	Approved
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6166	Phase 2
0.7613	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3620	Phase 2
0.7606	Intermediate Similarity	NPD4534	Discontinued
0.7606	Intermediate Similarity	NPD5958	Discontinued
0.7591	Intermediate Similarity	NPD3268	Approved
0.7578	Intermediate Similarity	NPD7157	Approved
0.7574	Intermediate Similarity	NPD2614	Approved
0.7561	Intermediate Similarity	NPD968	Approved
0.7557	Intermediate Similarity	NPD6516	Phase 2
0.7557	Intermediate Similarity	NPD5846	Approved
0.7556	Intermediate Similarity	NPD6584	Phase 3
0.7554	Intermediate Similarity	NPD447	Suspended
0.7536	Intermediate Similarity	NPD8032	Phase 2
0.7535	Intermediate Similarity	NPD2344	Approved
0.7518	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD8166	Discontinued
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7481	Intermediate Similarity	NPD5585	Approved
0.7465	Intermediate Similarity	NPD6099	Approved
0.7465	Intermediate Similarity	NPD6100	Approved
0.7465	Intermediate Similarity	NPD2935	Discontinued
0.7464	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1281	Approved
0.7434	Intermediate Similarity	NPD3817	Phase 2
0.7424	Intermediate Similarity	NPD2932	Approved
0.7424	Intermediate Similarity	NPD3019	Approved
0.7421	Intermediate Similarity	NPD7074	Phase 3
0.741	Intermediate Similarity	NPD2674	Phase 3
0.7403	Intermediate Similarity	NPD6234	Discontinued
0.7395	Intermediate Similarity	NPD2860	Approved
0.7395	Intermediate Similarity	NPD2859	Approved
0.7388	Intermediate Similarity	NPD3972	Approved
0.7379	Intermediate Similarity	NPD3750	Approved
0.7368	Intermediate Similarity	NPD1465	Phase 2
0.7358	Intermediate Similarity	NPD7054	Approved
0.7357	Intermediate Similarity	NPD943	Approved
0.7355	Intermediate Similarity	NPD3020	Approved
0.7353	Intermediate Similarity	NPD1203	Approved
0.7348	Intermediate Similarity	NPD1357	Approved
0.7343	Intermediate Similarity	NPD4477	Approved
0.7343	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4476	Approved
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7333	Intermediate Similarity	NPD6583	Phase 3
0.7333	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6582	Phase 2
0.7329	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD6190	Approved
0.7329	Intermediate Similarity	NPD2354	Approved
0.7313	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1610	Phase 2
0.7312	Intermediate Similarity	NPD7472	Approved
0.7311	Intermediate Similarity	NPD2934	Approved
0.7311	Intermediate Similarity	NPD2933	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7199	Phase 2
0.7299	Intermediate Similarity	NPD5647	Approved
0.7299	Intermediate Similarity	NPD2798	Approved
0.7297	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1778	Approved
0.7292	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7028	Phase 2
0.7279	Intermediate Similarity	NPD1876	Approved
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6331	Phase 2
0.7254	Intermediate Similarity	NPD6653	Approved
0.7241	Intermediate Similarity	NPD1549	Phase 2
0.7234	Intermediate Similarity	NPD825	Approved
0.7234	Intermediate Similarity	NPD2979	Phase 3
0.7234	Intermediate Similarity	NPD1240	Approved
0.7234	Intermediate Similarity	NPD826	Approved
0.7226	Intermediate Similarity	NPD3266	Approved
0.7226	Intermediate Similarity	NPD3267	Approved
0.7226	Intermediate Similarity	NPD987	Approved
0.7222	Intermediate Similarity	NPD2438	Suspended
0.7222	Intermediate Similarity	NPD6032	Approved
0.7222	Intermediate Similarity	NPD290	Approved
0.7219	Intermediate Similarity	NPD3455	Phase 2
0.7215	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3145	Approved
0.7214	Intermediate Similarity	NPD3144	Approved
0.7206	Intermediate Similarity	NPD4359	Approved
0.7206	Intermediate Similarity	NPD2982	Phase 2
0.7206	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4908	Phase 1
0.7192	Intermediate Similarity	NPD4162	Approved
0.719	Intermediate Similarity	NPD37	Approved
0.7183	Intermediate Similarity	NPD1933	Approved
0.7178	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD257	Approved
0.7174	Intermediate Similarity	NPD258	Approved
0.7172	Intermediate Similarity	NPD2346	Discontinued
0.7171	Intermediate Similarity	NPD4380	Phase 2
0.7167	Intermediate Similarity	NPD9296	Approved
0.7164	Intermediate Similarity	NPD4626	Approved
0.7161	Intermediate Similarity	NPD4967	Phase 2
0.7161	Intermediate Similarity	NPD4965	Approved
0.7161	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD6797	Phase 2
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3225	Approved
0.7153	Intermediate Similarity	NPD4308	Phase 3
0.7153	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7133	Intermediate Similarity	NPD5049	Phase 3
0.7133	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD2653	Approved
0.7133	Intermediate Similarity	NPD1607	Approved
0.7132	Intermediate Similarity	NPD2981	Phase 2
0.7132	Intermediate Similarity	NPD2231	Phase 2
0.7132	Intermediate Similarity	NPD2235	Phase 2
0.7123	Intermediate Similarity	NPD2424	Discontinued
0.7123	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3018	Phase 2
0.7117	Intermediate Similarity	NPD7251	Discontinued
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7115	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6799	Approved
0.7113	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4140	Approved
0.7111	Intermediate Similarity	NPD3496	Discontinued
0.7109	Intermediate Similarity	NPD5451	Approved
0.7105	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1519	Approved
0.7103	Intermediate Similarity	NPD2796	Approved
0.7103	Intermediate Similarity	NPD2161	Phase 2
0.7103	Intermediate Similarity	NPD1538	Phase 1
0.7103	Intermediate Similarity	NPD1537	Approved
0.7092	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5111	Phase 2
0.7092	Intermediate Similarity	NPD3764	Approved
0.7092	Intermediate Similarity	NPD5109	Approved
0.7092	Intermediate Similarity	NPD5110	Phase 2
0.7089	Intermediate Similarity	NPD8127	Discontinued
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.7081	Intermediate Similarity	NPD7228	Approved
0.708	Intermediate Similarity	NPD4749	Approved
0.7077	Intermediate Similarity	NPD821	Approved
0.7075	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3060	Approved
0.7073	Intermediate Similarity	NPD7808	Phase 3
0.7067	Intermediate Similarity	NPD3146	Approved
0.7067	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD230	Phase 1

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