NPASS Compound

Structure

NPC164244 OpenBabel07101718282D 30 34 0 0 1 0 0 0 0 0999 V2000 5.8915 1.5660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 2.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1097 0.9425 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.2769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 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 1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7207 0.9425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 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 11 1 0 0 0 0 4 12 1 0 0 0 0 7 27 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 1 1 1 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 2 1 6 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 5 1 6 0 0 0 13 28 1 0 0 0 0 14 6 1 1 0 0 0 14 30 1 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 29 1 0 0 0 0 22 18 1 6 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 24 27 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.19
Volume:	417.8
LogP:	5.671
LogD:	3.867
LogS:	-4.811
# Rotatable Bonds:	1
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	5.33
Fsp3:	0.542
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:	-4.727
MDCK Permeability:	1.6895954104256816e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.912
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.76
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	94.03638458251953%
Volume Distribution (VD):	1.464
Pgp-substrate:	5.428775310516357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.29
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.553
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	9.727
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.529
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.831
Carcinogencity:	0.394
Eye Corrosion:	0.131
Eye Irritation:	0.89
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC164244

Natural Product ID:	NPC164244
*Common Name:**	Penicitrinol F
IUPAC Name:	n.a.
Synonyms:	Penicitrinol F
Standard InCHIKey:	MYKUBENCMVPBLA-ZPLCETTNSA-N
Standard InCHI:	InChI=1S/C24H28O6/c1-9-13(5)28-22-18-16(8-15(25)11(3)17(9)18)29-21-12(4)20-10(2)14(6)30-24(20,27-7)23(26)19(21)22/h8-10,13-14,22,25H,1-7H3/t9-,10-,13-,14-,22-,24-/m1/s1
SMILES:	CO[C@@]12O[C@@H]([C@H](C1=C(C)C1=C(C2=O)[C@@H]2O[C@H](C)[C@H](c3c2c(O1)cc(c3C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822984
PubChem CID:	53466282
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
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]

☑ 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	3

Activity Type	# Activity
Cell Line	3

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[469649]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[469649]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[469649]

☑ 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 NPC164244 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	375
0.1-0.2	1470
0.2-0.3	3045
0.3-0.4	6951
0.4-0.5	11458
0.5-0.6	4851
0.6-0.7	6286
0.7-0.8	7658
0.8-0.85	588
0.85-0.9	10
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9156	High Similarity	NPC267242
0.9091	High Similarity	NPC60084
0.8909	High Similarity	NPC5671
0.8742	High Similarity	NPC125969
0.8704	High Similarity	NPC314653
0.8704	High Similarity	NPC316262
0.8688	High Similarity	NPC313368
0.8625	High Similarity	NPC264932
0.8625	High Similarity	NPC311574
0.8606	High Similarity	NPC477573
0.8606	High Similarity	NPC477571
0.8606	High Similarity	NPC477572
0.8581	High Similarity	NPC142863
0.8581	High Similarity	NPC259632
0.858	High Similarity	NPC475106
0.858	High Similarity	NPC310603
0.858	High Similarity	NPC472402
0.8571	High Similarity	NPC172687
0.8562	High Similarity	NPC470606
0.8562	High Similarity	NPC210048
0.8545	High Similarity	NPC259905
0.8544	High Similarity	NPC87708
0.8535	High Similarity	NPC472633
0.8528	High Similarity	NPC66087
0.8528	High Similarity	NPC278419
0.8528	High Similarity	NPC179198
0.8526	High Similarity	NPC470460
0.8521	High Similarity	NPC244903
0.8516	High Similarity	NPC290133
0.8516	High Similarity	NPC24136
0.8516	High Similarity	NPC187282
0.8509	High Similarity	NPC470607
0.8503	High Similarity	NPC470336
0.8503	High Similarity	NPC470335
0.85	High Similarity	NPC211482
0.85	High Similarity	NPC476652
0.8494	Intermediate Similarity	NPC313717
0.8494	Intermediate Similarity	NPC315306
0.8491	Intermediate Similarity	NPC311579
0.8491	Intermediate Similarity	NPC472799
0.8491	Intermediate Similarity	NPC236756
0.8481	Intermediate Similarity	NPC232645
0.8481	Intermediate Similarity	NPC72958
0.8481	Intermediate Similarity	NPC470675
0.8481	Intermediate Similarity	NPC473131
0.8471	Intermediate Similarity	NPC470461
0.8466	Intermediate Similarity	NPC473022
0.8466	Intermediate Similarity	NPC131745
0.8457	Intermediate Similarity	NPC306978
0.8457	Intermediate Similarity	NPC472618
0.8447	Intermediate Similarity	NPC161650
0.8447	Intermediate Similarity	NPC282390
0.8447	Intermediate Similarity	NPC246466
0.8447	Intermediate Similarity	NPC281137
0.8443	Intermediate Similarity	NPC223375
0.8443	Intermediate Similarity	NPC475825
0.8443	Intermediate Similarity	NPC91650
0.8442	Intermediate Similarity	NPC472610
0.8442	Intermediate Similarity	NPC204469
0.8438	Intermediate Similarity	NPC470605
0.8438	Intermediate Similarity	NPC470604
0.8438	Intermediate Similarity	NPC470603
0.8434	Intermediate Similarity	NPC470207
0.8434	Intermediate Similarity	NPC264063
0.8434	Intermediate Similarity	NPC470206
0.8434	Intermediate Similarity	NPC469486
0.8428	Intermediate Similarity	NPC288534
0.8424	Intermediate Similarity	NPC178851
0.8424	Intermediate Similarity	NPC62444
0.8424	Intermediate Similarity	NPC476255
0.8421	Intermediate Similarity	NPC470332
0.8418	Intermediate Similarity	NPC325983
0.8418	Intermediate Similarity	NPC476185
0.8418	Intermediate Similarity	NPC471115
0.8418	Intermediate Similarity	NPC321896
0.8418	Intermediate Similarity	NPC150928
0.8418	Intermediate Similarity	NPC29777
0.8415	Intermediate Similarity	NPC183672
0.8415	Intermediate Similarity	NPC290160
0.8411	Intermediate Similarity	NPC309452
0.8408	Intermediate Similarity	NPC296869
0.8408	Intermediate Similarity	NPC168085
0.8405	Intermediate Similarity	NPC18380
0.8405	Intermediate Similarity	NPC476929
0.8405	Intermediate Similarity	NPC312273
0.8405	Intermediate Similarity	NPC301256
0.8405	Intermediate Similarity	NPC117985
0.8405	Intermediate Similarity	NPC187354
0.8402	Intermediate Similarity	NPC475233
0.8397	Intermediate Similarity	NPC473135
0.8397	Intermediate Similarity	NPC306488
0.8397	Intermediate Similarity	NPC329678
0.8397	Intermediate Similarity	NPC470458
0.8397	Intermediate Similarity	NPC470676
0.8397	Intermediate Similarity	NPC5820
0.8397	Intermediate Similarity	NPC473132
0.8397	Intermediate Similarity	NPC178343
0.8395	Intermediate Similarity	NPC472617
0.8393	Intermediate Similarity	NPC229051
0.8393	Intermediate Similarity	NPC475080
0.8393	Intermediate Similarity	NPC131862
0.8393	Intermediate Similarity	NPC213052
0.8389	Intermediate Similarity	NPC24913
0.8389	Intermediate Similarity	NPC177712
0.8387	Intermediate Similarity	NPC158874
0.8385	Intermediate Similarity	NPC17521
0.8383	Intermediate Similarity	NPC298778
0.8375	Intermediate Similarity	NPC178964
0.8375	Intermediate Similarity	NPC268950
0.8375	Intermediate Similarity	NPC108706
0.8375	Intermediate Similarity	NPC95842
0.8375	Intermediate Similarity	NPC211158
0.8375	Intermediate Similarity	NPC87304
0.8375	Intermediate Similarity	NPC280530
0.8375	Intermediate Similarity	NPC193200
0.8375	Intermediate Similarity	NPC78021
0.8373	Intermediate Similarity	NPC150131
0.8373	Intermediate Similarity	NPC292233
0.8365	Intermediate Similarity	NPC290671
0.8365	Intermediate Similarity	NPC318424
0.8365	Intermediate Similarity	NPC325429
0.8363	Intermediate Similarity	NPC6709
0.8363	Intermediate Similarity	NPC170203
0.8355	Intermediate Similarity	NPC470209
0.8354	Intermediate Similarity	NPC473012
0.8354	Intermediate Similarity	NPC97028
0.8354	Intermediate Similarity	NPC139966
0.8354	Intermediate Similarity	NPC158338
0.8354	Intermediate Similarity	NPC97029
0.8354	Intermediate Similarity	NPC198927
0.8354	Intermediate Similarity	NPC211107
0.8354	Intermediate Similarity	NPC317492
0.8354	Intermediate Similarity	NPC100985
0.8354	Intermediate Similarity	NPC4423
0.8354	Intermediate Similarity	NPC307052
0.8354	Intermediate Similarity	NPC15374
0.8354	Intermediate Similarity	NPC473016
0.8354	Intermediate Similarity	NPC259834
0.8354	Intermediate Similarity	NPC125991
0.8354	Intermediate Similarity	NPC77325
0.8354	Intermediate Similarity	NPC288036
0.8354	Intermediate Similarity	NPC94796
0.8354	Intermediate Similarity	NPC65589
0.8354	Intermediate Similarity	NPC150164
0.8353	Intermediate Similarity	NPC246877
0.8353	Intermediate Similarity	NPC67302
0.8344	Intermediate Similarity	NPC43490
0.8344	Intermediate Similarity	NPC292863
0.8344	Intermediate Similarity	NPC308200
0.8344	Intermediate Similarity	NPC473077
0.8344	Intermediate Similarity	NPC296998
0.8344	Intermediate Similarity	NPC470810
0.8344	Intermediate Similarity	NPC184326
0.8344	Intermediate Similarity	NPC475107
0.8343	Intermediate Similarity	NPC474345
0.8343	Intermediate Similarity	NPC294629
0.8333	Intermediate Similarity	NPC326500
0.8333	Intermediate Similarity	NPC5029
0.8333	Intermediate Similarity	NPC473692
0.8333	Intermediate Similarity	NPC224714
0.8333	Intermediate Similarity	NPC470890
0.8333	Intermediate Similarity	NPC212697
0.8333	Intermediate Similarity	NPC272196
0.8333	Intermediate Similarity	NPC30432
0.8333	Intermediate Similarity	NPC271385
0.8333	Intermediate Similarity	NPC216538
0.8333	Intermediate Similarity	NPC111536
0.8333	Intermediate Similarity	NPC158542
0.8333	Intermediate Similarity	NPC118128
0.8333	Intermediate Similarity	NPC470674
0.8333	Intermediate Similarity	NPC271288
0.8333	Intermediate Similarity	NPC76128
0.8333	Intermediate Similarity	NPC245452
0.8333	Intermediate Similarity	NPC201127
0.8333	Intermediate Similarity	NPC470673
0.8333	Intermediate Similarity	NPC117716
0.8333	Intermediate Similarity	NPC273538
0.8333	Intermediate Similarity	NPC71210
0.8333	Intermediate Similarity	NPC196448
0.8323	Intermediate Similarity	NPC304207
0.8323	Intermediate Similarity	NPC73028
0.8323	Intermediate Similarity	NPC166054
0.8323	Intermediate Similarity	NPC111341
0.8323	Intermediate Similarity	NPC5319
0.8323	Intermediate Similarity	NPC217706
0.8323	Intermediate Similarity	NPC48579
0.8323	Intermediate Similarity	NPC207809
0.8323	Intermediate Similarity	NPC472344
0.8323	Intermediate Similarity	NPC304745
0.8323	Intermediate Similarity	NPC310340
0.8323	Intermediate Similarity	NPC473202
0.8323	Intermediate Similarity	NPC476169
0.8323	Intermediate Similarity	NPC259710
0.8323	Intermediate Similarity	NPC55662
0.8313	Intermediate Similarity	NPC471349
0.8313	Intermediate Similarity	NPC271681
0.8313	Intermediate Similarity	NPC474843
0.8313	Intermediate Similarity	NPC166067
0.8313	Intermediate Similarity	NPC113968
0.8313	Intermediate Similarity	NPC471347

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 NPC164244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	903
0.2-0.3	1889
0.3-0.4	2556
0.4-0.5	1969
0.5-0.6	999
0.6-0.7	375
0.7-0.8	131
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8148	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7819	Suspended
0.8118	Intermediate Similarity	NPD6797	Phase 2
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7075	Discontinued
0.8101	Intermediate Similarity	NPD2533	Approved
0.8101	Intermediate Similarity	NPD2532	Approved
0.8101	Intermediate Similarity	NPD2534	Approved
0.8098	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7251	Discontinued
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD3751	Discontinued
0.8037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8013	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD6801	Discontinued
0.7963	Intermediate Similarity	NPD4380	Phase 2
0.7941	Intermediate Similarity	NPD3818	Discontinued
0.7919	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3787	Discontinued
0.7904	Intermediate Similarity	NPD5494	Approved
0.7895	Intermediate Similarity	NPD7054	Approved
0.7885	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1934	Approved
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7849	Intermediate Similarity	NPD7074	Phase 3
0.7849	Intermediate Similarity	NPD7472	Approved
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD1549	Phase 2
0.7831	Intermediate Similarity	NPD3882	Suspended
0.7824	Intermediate Similarity	NPD6166	Phase 2
0.7824	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6099	Approved
0.7821	Intermediate Similarity	NPD6100	Approved
0.7805	Intermediate Similarity	NPD7411	Suspended
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD37	Approved
0.7738	Intermediate Similarity	NPD6234	Discontinued
0.7725	Intermediate Similarity	NPD4965	Approved
0.7725	Intermediate Similarity	NPD4966	Approved
0.7725	Intermediate Similarity	NPD4967	Phase 2
0.7716	Intermediate Similarity	NPD1512	Approved
0.7707	Intermediate Similarity	NPD2796	Approved
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7679	Intermediate Similarity	NPD3749	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD1510	Phase 2
0.763	Intermediate Similarity	NPD7228	Approved
0.7619	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2801	Approved
0.7602	Intermediate Similarity	NPD5710	Approved
0.7602	Intermediate Similarity	NPD5711	Approved
0.7602	Intermediate Similarity	NPD7229	Phase 3
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6799	Approved
0.7593	Intermediate Similarity	NPD1511	Approved
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7564	Intermediate Similarity	NPD5124	Phase 1
0.7564	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.756	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD3748	Approved
0.753	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7455	Intermediate Similarity	NPD5403	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7442	Intermediate Similarity	NPD1247	Approved
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7389	Intermediate Similarity	NPD1240	Approved
0.7389	Intermediate Similarity	NPD4060	Phase 1
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4749	Approved
0.7346	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5401	Approved
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7296	Intermediate Similarity	NPD1607	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7263	Intermediate Similarity	NPD7240	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7262	Intermediate Similarity	NPD3226	Approved
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7222	Intermediate Similarity	NPD6002	Phase 3
0.7222	Intermediate Similarity	NPD6004	Phase 3
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6005	Phase 3
0.7222	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2403	Approved
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4363	Phase 3
0.7204	Intermediate Similarity	NPD4360	Phase 2
0.7202	Intermediate Similarity	NPD1653	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7697	Approved
0.7169	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2797	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7134	Intermediate Similarity	NPD6674	Discontinued
0.7126	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7114	Intermediate Similarity	NPD8366	Approved
0.7099	Intermediate Similarity	NPD2799	Discontinued
0.7095	Intermediate Similarity	NPD7286	Phase 2
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7063	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1613	Approved
0.7062	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.7017	Intermediate Similarity	NPD5953	Discontinued
0.7012	Intermediate Similarity	NPD5762	Approved
0.7012	Intermediate Similarity	NPD2344	Approved
0.7012	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2798	Approved
0.7005	Intermediate Similarity	NPD7801	Approved
0.6988	Remote Similarity	NPD4628	Phase 3
0.6987	Remote Similarity	NPD6696	Suspended
0.6984	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4361	Phase 2
0.6982	Remote Similarity	NPD6273	Approved
0.6976	Remote Similarity	NPD8491	Approved
0.6974	Remote Similarity	NPD1548	Phase 1
0.6974	Remote Similarity	NPD7584	Approved
0.697	Remote Similarity	NPD2424	Discontinued
0.6968	Remote Similarity	NPD1608	Approved
0.6962	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8320	Phase 1
0.6959	Remote Similarity	NPD8319	Approved
0.6954	Remote Similarity	NPD4288	Approved
0.6943	Remote Similarity	NPD3267	Approved
0.6943	Remote Similarity	NPD3266	Approved
0.6942	Remote Similarity	NPD8469	Approved
0.6937	Remote Similarity	NPD2313	Discontinued
0.6928	Remote Similarity	NPD1652	Phase 2
0.6928	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7783	Phase 2
0.6919	Remote Similarity	NPD7028	Phase 2
0.6918	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD230	Phase 1
0.6911	Remote Similarity	NPD7700	Phase 2
0.6911	Remote Similarity	NPD7699	Phase 2
0.6909	Remote Similarity	NPD1471	Phase 3
0.6897	Remote Similarity	NPD5761	Phase 2
0.6897	Remote Similarity	NPD5760	Phase 2
0.6894	Remote Similarity	NPD6233	Phase 2

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