NPASS Compound

Structure

NPC246877 OpenBabel07101719252D 28 32 0 0 1 0 0 0 0 0999 V2000 4.0940 0.3410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -3.7601 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 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -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 3.1631 -0.0243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 0 0 2 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 3.1055 -0.7930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 2 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 0.5000 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 -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 0.8660 -1.5000 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 1.7321 -1.0000 0.0000 C 0 0 2 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -1.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 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 3 10 1 0 0 0 0 4 11 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 1 1 6 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 2 1 6 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 5 1 1 0 0 0 12 26 1 0 0 0 0 13 6 1 1 0 0 0 13 27 1 0 0 0 0 14 24 1 0 0 0 0 15 18 2 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 17 22 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 18 1 1 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.18
Volume:	391.714
LogP:	6.071
LogD:	3.547
LogS:	-5.362
# Rotatable Bonds:	0
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	4.858
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.995
MDCK Permeability:	2.2011587134329602e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.176
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	99.61476135253906%
Volume Distribution (VD):	1.83
Pgp-substrate:	2.0012803077697754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.584
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.417
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.248
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	1.667
Half-life (T1/2):	0.14

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.721
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.811
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.895
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC246877

Natural Product ID:	NPC246877
*Common Name:**	Penicitrinol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CRGUXPKRGKYBJY-ZUZBTREBSA-N
Standard InCHI:	InChI=1S/C23H26O5/c1-8-12(5)26-21-18-15(7-14(24)10(3)16(8)18)28-23-19(21)20(25)11(4)17-9(2)13(6)27-22(17)23/h7-9,12-13,21,24-25H,1-6H3/t8-,9-,12-,13-,21-/m1/s1
SMILES:	C[C@@H]1[C@@H](C)O[C@@H]2c3c(cc(c(C)c13)O)Oc1c2c(c(C)c2[C@H](C)[C@@H](C)Oc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457490
PubChem CID:	44567617
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO32513	Penicillium citrinum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18281952]
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]
NPO41450	Penicillium citrinum + Aspergillus sydowii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31953204]

☑ 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	4

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[500173]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[500173]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[500173]
NPT1	Others	Radical scavenging activity		IC50	=	26800.0	nM	PMID[500172]

☑ 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 NPC246877 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	468
0.1-0.2	1697
0.2-0.3	4383
0.3-0.4	11782
0.4-0.5	6719
0.5-0.6	3899
0.6-0.7	7213
0.7-0.8	5155
0.8-0.85	903
0.85-0.9	417
0.9-0.95	59
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC65885
0.9217	High Similarity	NPC25361
0.9157	High Similarity	NPC197168
0.9157	High Similarity	NPC273959
0.9123	High Similarity	NPC8127
0.9123	High Similarity	NPC49667
0.9112	High Similarity	NPC476641
0.9107	High Similarity	NPC45760
0.9064	High Similarity	NPC287243
0.9053	High Similarity	NPC242395
0.9053	High Similarity	NPC152477
0.9048	High Similarity	NPC128293
0.9023	High Similarity	NPC228209
0.9017	High Similarity	NPC104682
0.9017	High Similarity	NPC476273
0.9006	High Similarity	NPC82217
0.9006	High Similarity	NPC310794
0.9006	High Similarity	NPC216842
0.9006	High Similarity	NPC476640
0.8994	High Similarity	NPC150131
0.8988	High Similarity	NPC37183
0.8988	High Similarity	NPC326520
0.8988	High Similarity	NPC45449
0.8977	High Similarity	NPC240808
0.896	High Similarity	NPC5671
0.896	High Similarity	NPC23553
0.896	High Similarity	NPC77179
0.8947	High Similarity	NPC230619
0.8947	High Similarity	NPC121333
0.8947	High Similarity	NPC54098
0.8941	High Similarity	NPC247136
0.8935	High Similarity	NPC477517
0.8935	High Similarity	NPC472452
0.8935	High Similarity	NPC170245
0.8935	High Similarity	NPC173292
0.8935	High Similarity	NPC277480
0.8929	High Similarity	NPC133065
0.8922	High Similarity	NPC66288
0.8922	High Similarity	NPC474186
0.8914	High Similarity	NPC240508
0.8914	High Similarity	NPC8927
0.8914	High Similarity	NPC246153
0.8889	High Similarity	NPC102277
0.8889	High Similarity	NPC131866
0.8889	High Similarity	NPC279209
0.8889	High Similarity	NPC190351
0.8882	High Similarity	NPC247973
0.8882	High Similarity	NPC8965
0.8882	High Similarity	NPC6588
0.8882	High Similarity	NPC477154
0.8882	High Similarity	NPC474024
0.8882	High Similarity	NPC117854
0.8876	High Similarity	NPC295436
0.8876	High Similarity	NPC36320
0.8876	High Similarity	NPC234052
0.8876	High Similarity	NPC39306
0.8869	High Similarity	NPC238995
0.8869	High Similarity	NPC52204
0.8864	High Similarity	NPC476170
0.8862	High Similarity	NPC475886
0.8862	High Similarity	NPC298093
0.8862	High Similarity	NPC474287
0.8855	High Similarity	NPC217677
0.8855	High Similarity	NPC165977
0.8851	High Similarity	NPC221820
0.8844	High Similarity	NPC245975
0.8844	High Similarity	NPC227906
0.8837	High Similarity	NPC4200
0.883	High Similarity	NPC177480
0.883	High Similarity	NPC326877
0.8827	High Similarity	NPC60848
0.8824	High Similarity	NPC43319
0.8824	High Similarity	NPC272502
0.8824	High Similarity	NPC120593
0.8817	High Similarity	NPC270837
0.8817	High Similarity	NPC236132
0.8817	High Similarity	NPC59295
0.8817	High Similarity	NPC39305
0.8817	High Similarity	NPC263092
0.8817	High Similarity	NPC1706
0.8817	High Similarity	NPC236521
0.8817	High Similarity	NPC475985
0.8817	High Similarity	NPC248638
0.8817	High Similarity	NPC474240
0.8817	High Similarity	NPC152659
0.8817	High Similarity	NPC1755
0.881	High Similarity	NPC474351
0.881	High Similarity	NPC475883
0.881	High Similarity	NPC474187
0.8807	High Similarity	NPC150977
0.8802	High Similarity	NPC85121
0.88	High Similarity	NPC183843
0.8795	High Similarity	NPC45131
0.8795	High Similarity	NPC180924
0.8793	High Similarity	NPC156635
0.8786	High Similarity	NPC277510
0.8779	High Similarity	NPC472276
0.8779	High Similarity	NPC74559
0.8772	High Similarity	NPC218226
0.8772	High Similarity	NPC126204
0.8772	High Similarity	NPC225419
0.8772	High Similarity	NPC470704
0.8765	High Similarity	NPC224280
0.8765	High Similarity	NPC62261
0.8765	High Similarity	NPC293319
0.8765	High Similarity	NPC473286
0.8765	High Similarity	NPC475888
0.8757	High Similarity	NPC211107
0.8757	High Similarity	NPC220912
0.8757	High Similarity	NPC229632
0.8757	High Similarity	NPC272722
0.8757	High Similarity	NPC294965
0.8757	High Similarity	NPC472402
0.8757	High Similarity	NPC25152
0.8757	High Similarity	NPC15374
0.8757	High Similarity	NPC312056
0.8757	High Similarity	NPC84515
0.8757	High Similarity	NPC81679
0.875	High Similarity	NPC228785
0.875	High Similarity	NPC36217
0.875	High Similarity	NPC14353
0.875	High Similarity	NPC56085
0.875	High Similarity	NPC299436
0.8743	High Similarity	NPC223787
0.8743	High Similarity	NPC164110
0.8743	High Similarity	NPC67302
0.8743	High Similarity	NPC181960
0.8743	High Similarity	NPC246647
0.8743	High Similarity	NPC96342
0.8743	High Similarity	NPC212967
0.8736	High Similarity	NPC289244
0.8728	High Similarity	NPC174700
0.8728	High Similarity	NPC248593
0.8728	High Similarity	NPC28589
0.8727	High Similarity	NPC87708
0.8721	High Similarity	NPC300307
0.8721	High Similarity	NPC470207
0.8721	High Similarity	NPC475805
0.8721	High Similarity	NPC470206
0.8713	High Similarity	NPC37870
0.8706	High Similarity	NPC41301
0.8706	High Similarity	NPC473313
0.8706	High Similarity	NPC186686
0.8706	High Similarity	NPC205265
0.8706	High Similarity	NPC173587
0.8706	High Similarity	NPC472278
0.8706	High Similarity	NPC208120
0.8706	High Similarity	NPC329669
0.8706	High Similarity	NPC7483
0.8706	High Similarity	NPC146134
0.8706	High Similarity	NPC18100
0.8706	High Similarity	NPC472281
0.8698	High Similarity	NPC476929
0.8698	High Similarity	NPC188486
0.8698	High Similarity	NPC269117
0.8698	High Similarity	NPC45124
0.8698	High Similarity	NPC61010
0.8698	High Similarity	NPC30655
0.8698	High Similarity	NPC278052
0.8698	High Similarity	NPC74854
0.8698	High Similarity	NPC134783
0.8698	High Similarity	NPC40491
0.8698	High Similarity	NPC228383
0.8698	High Similarity	NPC474239
0.8693	High Similarity	NPC244903
0.8693	High Similarity	NPC473785
0.869	High Similarity	NPC196879
0.869	High Similarity	NPC473990
0.869	High Similarity	NPC186113
0.869	High Similarity	NPC100123
0.8678	High Similarity	NPC30550
0.8678	High Similarity	NPC149846
0.8678	High Similarity	NPC470335
0.8678	High Similarity	NPC470336
0.8671	High Similarity	NPC28042
0.8671	High Similarity	NPC315306
0.8671	High Similarity	NPC103307
0.8671	High Similarity	NPC101107
0.8671	High Similarity	NPC313717
0.8667	High Similarity	NPC232645
0.8667	High Similarity	NPC72958
0.8663	High Similarity	NPC50394
0.8663	High Similarity	NPC232936
0.8663	High Similarity	NPC476459
0.8663	High Similarity	NPC95715
0.8663	High Similarity	NPC470456
0.8659	High Similarity	NPC174486
0.8655	High Similarity	NPC275780
0.8655	High Similarity	NPC146584
0.8655	High Similarity	NPC316262
0.8655	High Similarity	NPC239752
0.8655	High Similarity	NPC303174
0.8655	High Similarity	NPC314653
0.8655	High Similarity	NPC472277
0.8655	High Similarity	NPC21016
0.8655	High Similarity	NPC470457
0.8655	High Similarity	NPC472450
0.8647	High Similarity	NPC474033
0.8647	High Similarity	NPC476247
0.8647	High Similarity	NPC474034

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 NPC246877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	951
0.2-0.3	1964
0.3-0.4	2779
0.4-0.5	1524
0.5-0.6	857
0.6-0.7	567
0.7-0.8	118
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8862	High Similarity	NPD5494	Approved
0.8721	High Similarity	NPD5844	Phase 1
0.8698	High Similarity	NPD6959	Discontinued
0.8547	High Similarity	NPD6166	Phase 2
0.8547	High Similarity	NPD6168	Clinical (unspecified phase)
0.8547	High Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD1934	Approved
0.8391	Intermediate Similarity	NPD7473	Discontinued
0.8372	Intermediate Similarity	NPD1247	Approved
0.8324	Intermediate Similarity	NPD6232	Discontinued
0.8258	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD2801	Approved
0.8198	Intermediate Similarity	NPD7075	Discontinued
0.815	Intermediate Similarity	NPD919	Approved
0.8129	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD7808	Phase 3
0.8111	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6797	Phase 2
0.8084	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD3817	Phase 2
0.8081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD3926	Phase 2
0.8059	Intermediate Similarity	NPD4380	Phase 2
0.8056	Intermediate Similarity	NPD7251	Discontinued
0.8045	Intermediate Similarity	NPD7074	Phase 3
0.8035	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD3818	Discontinued
0.8023	Intermediate Similarity	NPD7819	Suspended
0.8023	Intermediate Similarity	NPD1465	Phase 2
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3749	Approved
0.7989	Intermediate Similarity	NPD7054	Approved
0.7965	Intermediate Similarity	NPD6801	Discontinued
0.7944	Intermediate Similarity	NPD7472	Approved
0.7929	Intermediate Similarity	NPD1512	Approved
0.7901	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2533	Approved
0.787	Intermediate Similarity	NPD2532	Approved
0.787	Intermediate Similarity	NPD2534	Approved
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6599	Discontinued
0.7831	Intermediate Similarity	NPD1549	Phase 2
0.7811	Intermediate Similarity	NPD1511	Approved
0.7803	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5402	Approved
0.7765	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6799	Approved
0.7688	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD3751	Discontinued
0.7627	Intermediate Similarity	NPD7768	Phase 2
0.7605	Intermediate Similarity	NPD2796	Approved
0.7602	Intermediate Similarity	NPD7390	Discontinued
0.7581	Intermediate Similarity	NPD8312	Approved
0.7581	Intermediate Similarity	NPD8313	Approved
0.7574	Intermediate Similarity	NPD2800	Approved
0.7572	Intermediate Similarity	NPD920	Approved
0.7557	Intermediate Similarity	NPD37	Approved
0.7553	Intermediate Similarity	NPD8434	Phase 2
0.7545	Intermediate Similarity	NPD1510	Phase 2
0.7542	Intermediate Similarity	NPD6234	Discontinued
0.7541	Intermediate Similarity	NPD7228	Approved
0.753	Intermediate Similarity	NPD1607	Approved
0.7528	Intermediate Similarity	NPD4967	Phase 2
0.7528	Intermediate Similarity	NPD4966	Approved
0.7528	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3787	Discontinued
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7486	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5403	Approved
0.7471	Intermediate Similarity	NPD1243	Approved
0.7462	Intermediate Similarity	NPD7698	Approved
0.7462	Intermediate Similarity	NPD7697	Approved
0.7462	Intermediate Similarity	NPD7696	Phase 3
0.7462	Intermediate Similarity	NPD7435	Discontinued
0.746	Intermediate Similarity	NPD8150	Discontinued
0.7459	Intermediate Similarity	NPD7199	Phase 2
0.7456	Intermediate Similarity	NPD2344	Approved
0.745	Intermediate Similarity	NPD8151	Discontinued
0.744	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3750	Approved
0.7424	Intermediate Similarity	NPD7870	Phase 2
0.7424	Intermediate Similarity	NPD7871	Phase 2
0.7418	Intermediate Similarity	NPD5711	Approved
0.7418	Intermediate Similarity	NPD5710	Approved
0.741	Intermediate Similarity	NPD1240	Approved
0.7398	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2935	Discontinued
0.7396	Intermediate Similarity	NPD6100	Approved
0.7396	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD3226	Approved
0.7371	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5401	Approved
0.7353	Intermediate Similarity	NPD2346	Discontinued
0.7341	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7701	Phase 2
0.7291	Intermediate Similarity	NPD7783	Phase 2
0.7291	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2309	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1471	Phase 3
0.7249	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD6535	Approved
0.7231	Intermediate Similarity	NPD6534	Approved
0.7228	Intermediate Similarity	NPD7229	Phase 3
0.7225	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4628	Phase 3
0.7225	Intermediate Similarity	NPD7907	Approved
0.7212	Intermediate Similarity	NPD4111	Phase 1
0.7212	Intermediate Similarity	NPD4665	Approved
0.7208	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7700	Phase 2
0.7206	Intermediate Similarity	NPD7801	Approved
0.7196	Intermediate Similarity	NPD7240	Approved
0.7193	Intermediate Similarity	NPD1551	Phase 2
0.7186	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2403	Approved
0.715	Intermediate Similarity	NPD3057	Approved
0.7135	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD4625	Phase 3
0.7118	Intermediate Similarity	NPD6651	Approved
0.7113	Intermediate Similarity	NPD4287	Approved
0.7102	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1613	Approved
0.7101	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD943	Approved
0.7093	Intermediate Similarity	NPD5405	Approved
0.7093	Intermediate Similarity	NPD5404	Approved
0.7093	Intermediate Similarity	NPD5408	Approved
0.7093	Intermediate Similarity	NPD5406	Approved
0.7083	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8320	Phase 1
0.7079	Intermediate Similarity	NPD8319	Approved
0.7074	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4908	Phase 1
0.7065	Intermediate Similarity	NPD2972	Approved
0.7065	Intermediate Similarity	NPD3533	Approved
0.7065	Intermediate Similarity	NPD6823	Phase 2
0.7056	Intermediate Similarity	NPD4363	Phase 3
0.7056	Intermediate Similarity	NPD4360	Phase 2
0.7052	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7286	Phase 2
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7033	Intermediate Similarity	NPD5761	Phase 2
0.7033	Intermediate Similarity	NPD5760	Phase 2
0.7029	Intermediate Similarity	NPD7003	Approved
0.7015	Intermediate Similarity	NPD2493	Approved
0.7015	Intermediate Similarity	NPD2494	Approved
0.7006	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7458	Discontinued
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6995	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4583	Approved
0.6995	Remote Similarity	NPD4582	Approved
0.699	Remote Similarity	NPD2490	Approved
0.699	Remote Similarity	NPD2488	Approved
0.6989	Remote Similarity	NPD6190	Approved
0.6989	Remote Similarity	NPD8127	Discontinued
0.6985	Remote Similarity	NPD2974	Approved
0.6985	Remote Similarity	NPD2973	Approved
0.6985	Remote Similarity	NPD2975	Approved
0.6984	Remote Similarity	NPD7177	Discontinued
0.6984	Remote Similarity	NPD2163	Approved
0.6981	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2491	Approved
0.6971	Remote Similarity	NPD6674	Discontinued
0.6965	Remote Similarity	NPD4580	Approved
0.6965	Remote Similarity	NPD4107	Approved
0.6964	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5953	Discontinued
0.6959	Remote Similarity	NPD230	Phase 1
0.6959	Remote Similarity	NPD447	Suspended
0.6957	Remote Similarity	NPD5676	Approved
0.6946	Remote Similarity	NPD4004	Approved
0.6946	Remote Similarity	NPD4002	Approved
0.6944	Remote Similarity	NPD1653	Approved
0.6931	Remote Similarity	NPD3450	Approved
0.6931	Remote Similarity	NPD3452	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