NPASS Compound

Structure

NPC67424 OpenBabel07101719132D 33 36 0 0 1 0 0 0 0 0999 V2000 2.5981 -4.5000 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -3.4641 -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 -4.5000 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 -2.5981 -0.5000 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 -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 -3.0000 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 -1.7321 -2.0000 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 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 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 0.0000 1.0000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 22 1 0 0 0 0 19 28 1 1 0 0 0 20 24 1 0 0 0 0 20 29 1 1 0 0 0 21 32 1 0 0 0 0 22 23 1 6 0 0 0 22 33 1 0 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 6 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.13
Volume:	442.182
LogP:	2.614
LogD:	1.547
LogS:	-3.923
# Rotatable Bonds:	5
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	3.698
Fsp3:	0.208
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.407
MDCK Permeability:	6.811374987591989e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.075
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.676

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	100.45822143554688%
Volume Distribution (VD):	0.486
Pgp-substrate:	0.8555060029029846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.311
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	0.826
Half-life (T1/2):	0.742

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.141
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC67424

Natural Product ID:	NPC67424
*Common Name:**	[1',1'':1,4'-Terphenyl]-2',3',5'-Triol 2'-O-Beta-Glucuronide
IUPAC Name:	(2S,3S,4S,5R,6S)-6-(2,4-dihydroxy-3,6-diphenylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	QQDLPJHEFJKVHT-MJRVOHGCSA-N
Standard InCHI:	InChI=1S/C24H22O9/c25-15-11-14(12-7-3-1-4-8-12)21(17(26)16(15)13-9-5-2-6-10-13)32-24-20(29)18(27)19(28)22(33-24)23(30)31/h1-11,18-20,22,24-29H,(H,30,31)/p-1/t18-,19-,20+,22-,24+/m0/s1
SMILES:	c1ccc(cc1)c1cc(c(c2ccccc2)c(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3120853
PubChem CID:	24123416
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO32822	Streptomyces sp. LZ35	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24490633]
NPO32822	Streptomyces sp. LZ35	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24507923]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	IZ	=	11.2	mm	PMID[465766]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	15.8	mm	PMID[465766]

☑ 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 NPC67424 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	409
0.1-0.2	1796
0.2-0.3	4039
0.3-0.4	9700
0.4-0.5	8558
0.5-0.6	4921
0.6-0.7	6298
0.7-0.8	5850
0.8-0.85	897
0.85-0.9	227
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC265214
0.8994	High Similarity	NPC268533
0.8935	High Similarity	NPC115760
0.8935	High Similarity	NPC43211
0.8935	High Similarity	NPC135277
0.8935	High Similarity	NPC49344
0.8935	High Similarity	NPC210094
0.8935	High Similarity	NPC101191
0.8935	High Similarity	NPC237435
0.8895	High Similarity	NPC36138
0.8882	High Similarity	NPC472385
0.8882	High Similarity	NPC472380
0.8882	High Similarity	NPC198324
0.8882	High Similarity	NPC472384
0.8882	High Similarity	NPC472382
0.8848	High Similarity	NPC55121
0.8844	High Similarity	NPC470416
0.883	High Similarity	NPC476620
0.883	High Similarity	NPC476622
0.883	High Similarity	NPC476623
0.883	High Similarity	NPC476618
0.883	High Similarity	NPC476619
0.883	High Similarity	NPC476621
0.8827	High Similarity	NPC142479
0.8827	High Similarity	NPC155015
0.8824	High Similarity	NPC264735
0.8824	High Similarity	NPC477848
0.882	High Similarity	NPC78809
0.8772	High Similarity	NPC472992
0.8772	High Similarity	NPC61904
0.8772	High Similarity	NPC472991
0.8772	High Similarity	NPC233994
0.8772	High Similarity	NPC144097
0.8772	High Similarity	NPC211532
0.8765	High Similarity	NPC24043
0.8765	High Similarity	NPC62903
0.8765	High Similarity	NPC45522
0.8765	High Similarity	NPC101026
0.8765	High Similarity	NPC4390
0.8765	High Similarity	NPC42773
0.8765	High Similarity	NPC169977
0.8765	High Similarity	NPC21666
0.8765	High Similarity	NPC7178
0.8757	High Similarity	NPC204937
0.8757	High Similarity	NPC84265
0.8757	High Similarity	NPC282987
0.8757	High Similarity	NPC155763
0.8757	High Similarity	NPC245014
0.8757	High Similarity	NPC149011
0.8757	High Similarity	NPC235260
0.8757	High Similarity	NPC20505
0.8735	High Similarity	NPC174311
0.8728	High Similarity	NPC222674
0.8721	High Similarity	NPC168584
0.8721	High Similarity	NPC139571
0.8721	High Similarity	NPC37668
0.8721	High Similarity	NPC217520
0.8721	High Similarity	NPC253521
0.8721	High Similarity	NPC113836
0.8721	High Similarity	NPC35167
0.8721	High Similarity	NPC472387
0.8713	High Similarity	NPC214621
0.8713	High Similarity	NPC223426
0.8713	High Similarity	NPC34267
0.8713	High Similarity	NPC81042
0.8706	High Similarity	NPC175107
0.8706	High Similarity	NPC476405
0.8706	High Similarity	NPC472386
0.8706	High Similarity	NPC254540
0.8706	High Similarity	NPC190003
0.8706	High Similarity	NPC153755
0.8706	High Similarity	NPC172807
0.8706	High Similarity	NPC211594
0.8706	High Similarity	NPC117260
0.8704	High Similarity	NPC476154
0.8698	High Similarity	NPC170675
0.8698	High Similarity	NPC112755
0.8698	High Similarity	NPC471457
0.8698	High Similarity	NPC138927
0.8686	High Similarity	NPC261623
0.8686	High Similarity	NPC111490
0.8678	High Similarity	NPC470447
0.8678	High Similarity	NPC470446
0.8678	High Similarity	NPC470449
0.8678	High Similarity	NPC107987
0.8678	High Similarity	NPC470445
0.8675	High Similarity	NPC217950
0.8663	High Similarity	NPC154741
0.8663	High Similarity	NPC8573
0.8663	High Similarity	NPC296018
0.8663	High Similarity	NPC79736
0.8663	High Similarity	NPC67629
0.8655	High Similarity	NPC175230
0.8655	High Similarity	NPC88560
0.8655	High Similarity	NPC172033
0.8647	High Similarity	NPC21190
0.8647	High Similarity	NPC183357
0.8647	High Similarity	NPC244776
0.8647	High Similarity	NPC116864
0.8647	High Similarity	NPC22195
0.8647	High Similarity	NPC34287
0.8647	High Similarity	NPC471416
0.8639	High Similarity	NPC58716
0.8639	High Similarity	NPC45618
0.8639	High Similarity	NPC160156
0.8639	High Similarity	NPC92565
0.8639	High Similarity	NPC146792
0.8629	High Similarity	NPC470451
0.8629	High Similarity	NPC470455
0.8623	High Similarity	NPC90905
0.8623	High Similarity	NPC4013
0.8623	High Similarity	NPC192258
0.8623	High Similarity	NPC476200
0.8613	High Similarity	NPC477895
0.8613	High Similarity	NPC267549
0.8613	High Similarity	NPC217387
0.8613	High Similarity	NPC293626
0.8613	High Similarity	NPC196127
0.8613	High Similarity	NPC258044
0.8613	High Similarity	NPC476773
0.8613	High Similarity	NPC267680
0.8605	High Similarity	NPC253685
0.8596	High Similarity	NPC307518
0.8596	High Similarity	NPC67134
0.8596	High Similarity	NPC205076
0.8596	High Similarity	NPC48773
0.8596	High Similarity	NPC47140
0.8588	High Similarity	NPC475942
0.8588	High Similarity	NPC120099
0.8588	High Similarity	NPC223747
0.8588	High Similarity	NPC203050
0.8588	High Similarity	NPC93337
0.8588	High Similarity	NPC95855
0.8588	High Similarity	NPC210042
0.8588	High Similarity	NPC472381
0.8588	High Similarity	NPC219904
0.8588	High Similarity	NPC225434
0.8588	High Similarity	NPC472383
0.8588	High Similarity	NPC469931
0.8588	High Similarity	NPC45638
0.8588	High Similarity	NPC205721
0.8588	High Similarity	NPC52382
0.8588	High Similarity	NPC226294
0.8588	High Similarity	NPC270578
0.8588	High Similarity	NPC58053
0.8588	High Similarity	NPC105025
0.8588	High Similarity	NPC186807
0.8588	High Similarity	NPC201292
0.858	High Similarity	NPC197285
0.858	High Similarity	NPC118284
0.858	High Similarity	NPC145038
0.858	High Similarity	NPC469650
0.858	High Similarity	NPC179950
0.858	High Similarity	NPC21100
0.858	High Similarity	NPC274618
0.858	High Similarity	NPC276222
0.858	High Similarity	NPC281131
0.858	High Similarity	NPC253662
0.858	High Similarity	NPC56077
0.858	High Similarity	NPC308404
0.858	High Similarity	NPC88789
0.8571	High Similarity	NPC135831
0.8571	High Similarity	NPC127415
0.8571	High Similarity	NPC470718
0.8571	High Similarity	NPC297503
0.8571	High Similarity	NPC97119
0.8563	High Similarity	NPC473571
0.8563	High Similarity	NPC126784
0.8563	High Similarity	NPC124747
0.8563	High Similarity	NPC470443
0.8563	High Similarity	NPC470444
0.8563	High Similarity	NPC110941
0.8563	High Similarity	NPC155754
0.8563	High Similarity	NPC241423
0.8563	High Similarity	NPC473682
0.8555	High Similarity	NPC470949
0.8555	High Similarity	NPC297574
0.8555	High Similarity	NPC169733
0.8555	High Similarity	NPC65563
0.8554	High Similarity	NPC472156
0.8547	High Similarity	NPC51774
0.8547	High Similarity	NPC236191
0.8547	High Similarity	NPC239549
0.8547	High Similarity	NPC472993
0.8545	High Similarity	NPC165483
0.8539	High Similarity	NPC93065
0.8539	High Similarity	NPC472720
0.8539	High Similarity	NPC472721
0.8539	High Similarity	NPC469652
0.8539	High Similarity	NPC472724
0.8539	High Similarity	NPC201814
0.8539	High Similarity	NPC160543
0.8539	High Similarity	NPC31208
0.8538	High Similarity	NPC72249
0.8538	High Similarity	NPC44558
0.8538	High Similarity	NPC206123
0.8538	High Similarity	NPC224462
0.8538	High Similarity	NPC474434
0.8538	High Similarity	NPC105511
0.8531	High Similarity	NPC105591

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 NPC67424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	930
0.2-0.3	1990
0.3-0.4	2732
0.4-0.5	1772
0.5-0.6	894
0.6-0.7	340
0.7-0.8	105
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8935	High Similarity	NPD4338	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8324	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8304	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6166	Phase 2
0.8294	Intermediate Similarity	NPD3787	Discontinued
0.8286	Intermediate Similarity	NPD7808	Phase 3
0.8266	Intermediate Similarity	NPD7054	Approved
0.8266	Intermediate Similarity	NPD5844	Phase 1
0.8246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7472	Approved
0.8208	Intermediate Similarity	NPD7228	Approved
0.8129	Intermediate Similarity	NPD7199	Phase 2
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1653	Approved
0.8118	Intermediate Similarity	NPD6234	Discontinued
0.8103	Intermediate Similarity	NPD3751	Discontinued
0.8068	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7977	Intermediate Similarity	NPD6232	Discontinued
0.7955	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3817	Phase 2
0.7939	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1934	Approved
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7882	Intermediate Similarity	NPD2801	Approved
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7473	Discontinued
0.7833	Intermediate Similarity	NPD8313	Approved
0.7833	Intermediate Similarity	NPD8312	Approved
0.7814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD8455	Phase 2
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6190	Approved
0.7746	Intermediate Similarity	NPD7075	Discontinued
0.7722	Intermediate Similarity	NPD7240	Approved
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7688	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1613	Approved
0.7633	Intermediate Similarity	NPD5403	Approved
0.7574	Intermediate Similarity	NPD1512	Approved
0.7572	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5494	Approved
0.7539	Intermediate Similarity	NPD6780	Approved
0.7539	Intermediate Similarity	NPD6776	Approved
0.7539	Intermediate Similarity	NPD6781	Approved
0.7539	Intermediate Similarity	NPD6782	Approved
0.7539	Intermediate Similarity	NPD6779	Approved
0.7539	Intermediate Similarity	NPD6777	Approved
0.7539	Intermediate Similarity	NPD6778	Approved
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7514	Intermediate Similarity	NPD6959	Discontinued
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1511	Approved
0.7456	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7685	Pre-registration
0.7427	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6674	Discontinued
0.7423	Intermediate Similarity	NPD7680	Approved
0.7411	Intermediate Similarity	NPD8151	Discontinued
0.741	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD6233	Phase 2
0.7396	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7411	Suspended
0.7353	Intermediate Similarity	NPD6799	Approved
0.7346	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD7697	Approved
0.7333	Intermediate Similarity	NPD7698	Approved
0.733	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7033	Discontinued
0.7277	Intermediate Similarity	NPD6534	Approved
0.7277	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.7247	Intermediate Similarity	NPD3749	Approved
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7241	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7215	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7768	Phase 2
0.7184	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD7700	Phase 2
0.7164	Intermediate Similarity	NPD7801	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1247	Approved
0.7121	Intermediate Similarity	NPD8319	Approved
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.7111	Intermediate Similarity	NPD919	Approved
0.7108	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD6823	Phase 2
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7073	Intermediate Similarity	NPD4625	Phase 3
0.7053	Intermediate Similarity	NPD8434	Phase 2
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7045	Intermediate Similarity	NPD3226	Approved
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.7011	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2532	Approved
0.7011	Intermediate Similarity	NPD2533	Approved
0.7011	Intermediate Similarity	NPD2534	Approved
0.7006	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6978	Remote Similarity	NPD6746	Phase 2
0.6977	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3750	Approved
0.697	Remote Similarity	NPD7095	Approved
0.6959	Remote Similarity	NPD6213	Phase 3
0.6959	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6212	Phase 3
0.6951	Remote Similarity	NPD2861	Phase 2
0.694	Remote Similarity	NPD8127	Discontinued
0.6939	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7097	Phase 1
0.6914	Remote Similarity	NPD4749	Approved
0.6905	Remote Similarity	NPD230	Phase 1
0.6905	Remote Similarity	NPD447	Suspended
0.6894	Remote Similarity	NPD1610	Phase 2
0.6884	Remote Similarity	NPD3450	Approved
0.6884	Remote Similarity	NPD2494	Approved
0.6884	Remote Similarity	NPD3452	Approved
0.6884	Remote Similarity	NPD2493	Approved
0.6882	Remote Similarity	NPD1510	Phase 2
0.6872	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7458	Discontinued
0.6852	Remote Similarity	NPD1608	Approved
0.6842	Remote Similarity	NPD2796	Approved
0.6842	Remote Similarity	NPD2935	Discontinued
0.6826	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4002	Approved
0.6816	Remote Similarity	NPD4004	Approved
0.6802	Remote Similarity	NPD2346	Discontinued
0.6782	Remote Similarity	NPD4582	Approved
0.6782	Remote Similarity	NPD4583	Approved
0.6782	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4110	Phase 3
0.678	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1778	Approved
0.6768	Remote Similarity	NPD3225	Approved
0.6765	Remote Similarity	NPD1607	Approved
0.6749	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD943	Approved
0.6727	Remote Similarity	NPD2797	Approved
0.6726	Remote Similarity	NPD3268	Approved
0.6724	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1652	Phase 2
0.6723	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7584	Approved
0.6706	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5124	Phase 1
0.6686	Remote Similarity	NPD4062	Phase 3
0.6686	Remote Similarity	NPD3748	Approved
0.6684	Remote Similarity	NPD2490	Approved
0.6684	Remote Similarity	NPD2488	Approved
0.6683	Remote Similarity	NPD2974	Approved
0.6683	Remote Similarity	NPD7585	Approved
0.6683	Remote Similarity	NPD2975	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