NPASS Compound

Structure

NPC91650 OpenBabel07101718272D 31 34 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3424 3.3750 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.0860 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5605 2.7515 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 3.0860 0.0000 C 0 0 2 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 0.5000 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 2.5981 0.5000 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 1.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 2.7515 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 15 2 0 0 0 0 7 16 1 0 0 0 0 8 25 2 0 0 0 0 8 29 1 0 0 0 0 9 1 1 1 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 2 1 6 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 5 1 6 0 0 0 13 29 1 0 0 0 0 14 6 1 1 0 0 0 14 30 1 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 27 2 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 23 19 1 1 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.17
Volume:	429.874
LogP:	4.312
LogD:	2.689
LogS:	-4.253
# Rotatable Bonds:	3
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.968
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.062
MDCK Permeability:	1.0885229130508378e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.422
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.33647155761719%
Volume Distribution (VD):	0.627
Pgp-substrate:	2.5110514163970947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.268
CYP2C19-substrate:	0.254
CYP2C9-inhibitor:	0.617
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.233
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.36

ADMET: Excretion

Clearance (CL):	2.414
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.198
Carcinogencity:	0.843
Eye Corrosion:	0.003
Eye Irritation:	0.322
Respiratory Toxicity:	0.677

Download Data

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

Natural Product: NPC91650

Natural Product ID:	NPC91650
*Common Name:**	Citrinin H1
IUPAC Name:	n.a.
Synonyms:	Citrinin H1
Standard InCHIKey:	DPWQFCNWSJVFTQ-XYSRGHDZSA-N
Standard InCHI:	InChI=1S/C24H26O7/c1-9(13(5)29-8-25)18-12(4)21(27)20-23-19-16(31-24(20)22(18)28)7-15(26)11(3)17(19)10(2)14(6)30-23/h7-10,13-14,23,26H,1-6H3/t9-,10-,13-,14-,23-/m1/s1
SMILES:	C[C@H]([C@@H](C)OC=O)C1=C(C)C(=O)C2=C(C1=O)Oc1cc(c(C)c3[C@H](C)[C@@H](C)O[C@@H]2c13)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464673
PubChem CID:	44567621
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]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	=	32400.0	nM	PMID[527481]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	20900.0	nM	PMID[527481]
NPT81	Cell Line	A549	Homo sapiens	Activity	<	50.0	%	PMID[527481]
NPT1668	Cell Line	NCI-H157	Homo sapiens	Activity	<	50.0	%	PMID[527481]
NPT1	Others	Radical scavenging activity		IC50	=	58700.0	nM	PMID[527480]

☑ 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 NPC91650 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	371
0.1-0.2	1510
0.2-0.3	3500
0.3-0.4	7716
0.4-0.5	10647
0.5-0.6	4348
0.6-0.7	5993
0.7-0.8	7407
0.8-0.85	1181
0.85-0.9	22
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC5671
0.8957	High Similarity	NPC201127
0.8841	High Similarity	NPC474637
0.8817	High Similarity	NPC470206
0.8817	High Similarity	NPC470207
0.8743	High Similarity	NPC473022
0.8712	High Similarity	NPC87708
0.865	High Similarity	NPC72958
0.865	High Similarity	NPC232645
0.8639	High Similarity	NPC314653
0.8639	High Similarity	NPC316262
0.8623	High Similarity	NPC313368
0.8621	High Similarity	NPC246877
0.8598	High Similarity	NPC154683
0.8598	High Similarity	NPC40356
0.8588	High Similarity	NPC125465
0.8588	High Similarity	NPC476255
0.858	High Similarity	NPC109180
0.8563	High Similarity	NPC472661
0.8555	High Similarity	NPC154986
0.8545	High Similarity	NPC472799
0.8545	High Similarity	NPC214632
0.8538	High Similarity	NPC95715
0.8537	High Similarity	NPC230848
0.8529	High Similarity	NPC136641
0.8521	High Similarity	NPC193998
0.8521	High Similarity	NPC15374
0.8521	High Similarity	NPC94796
0.8514	High Similarity	NPC477682
0.8514	High Similarity	NPC477683
0.8512	High Similarity	NPC475107
0.8512	High Similarity	NPC472618
0.8512	High Similarity	NPC43490
0.8509	High Similarity	NPC28632
0.8509	High Similarity	NPC473692
0.8506	High Similarity	NPC86809
0.8506	High Similarity	NPC98667
0.8506	High Similarity	NPC232412
0.8503	High Similarity	NPC263483
0.8497	Intermediate Similarity	NPC472620
0.8497	Intermediate Similarity	NPC473113
0.8488	Intermediate Similarity	NPC472619
0.848	Intermediate Similarity	NPC62444
0.848	Intermediate Similarity	NPC477835
0.848	Intermediate Similarity	NPC472895
0.8476	Intermediate Similarity	NPC470568
0.8476	Intermediate Similarity	NPC150928
0.8471	Intermediate Similarity	NPC155640
0.8471	Intermediate Similarity	NPC290160
0.8466	Intermediate Similarity	NPC473785
0.8462	Intermediate Similarity	NPC18380
0.8457	Intermediate Similarity	NPC469345
0.8457	Intermediate Similarity	NPC473132
0.8457	Intermediate Similarity	NPC470676
0.8457	Intermediate Similarity	NPC473135
0.8452	Intermediate Similarity	NPC125969
0.8452	Intermediate Similarity	NPC474373
0.8452	Intermediate Similarity	NPC195167
0.8452	Intermediate Similarity	NPC186113
0.8448	Intermediate Similarity	NPC472054
0.8448	Intermediate Similarity	NPC475080
0.8443	Intermediate Similarity	NPC164244
0.8443	Intermediate Similarity	NPC472050
0.8443	Intermediate Similarity	NPC180924
0.8439	Intermediate Similarity	NPC315306
0.8439	Intermediate Similarity	NPC313717
0.8439	Intermediate Similarity	NPC477573
0.8439	Intermediate Similarity	NPC477571
0.8439	Intermediate Similarity	NPC241874
0.8439	Intermediate Similarity	NPC193698
0.8439	Intermediate Similarity	NPC477572
0.8434	Intermediate Similarity	NPC208806
0.843	Intermediate Similarity	NPC193222
0.8424	Intermediate Similarity	NPC312549
0.8424	Intermediate Similarity	NPC209142
0.8424	Intermediate Similarity	NPC149526
0.8424	Intermediate Similarity	NPC474417
0.8424	Intermediate Similarity	NPC470569
0.8415	Intermediate Similarity	NPC288036
0.8415	Intermediate Similarity	NPC4423
0.8415	Intermediate Similarity	NPC214493
0.8415	Intermediate Similarity	NPC80370
0.8415	Intermediate Similarity	NPC65589
0.8415	Intermediate Similarity	NPC97029
0.8415	Intermediate Similarity	NPC77325
0.8415	Intermediate Similarity	NPC158338
0.8415	Intermediate Similarity	NPC100985
0.8415	Intermediate Similarity	NPC473016
0.8415	Intermediate Similarity	NPC97028
0.8412	Intermediate Similarity	NPC475106
0.8402	Intermediate Similarity	NPC292863
0.8402	Intermediate Similarity	NPC260296
0.8402	Intermediate Similarity	NPC115432
0.8402	Intermediate Similarity	NPC184326
0.8402	Intermediate Similarity	NPC243701
0.84	Intermediate Similarity	NPC289244
0.84	Intermediate Similarity	NPC294149
0.84	Intermediate Similarity	NPC245975
0.84	Intermediate Similarity	NPC68381
0.84	Intermediate Similarity	NPC474345
0.8393	Intermediate Similarity	NPC164110
0.8393	Intermediate Similarity	NPC246647
0.8393	Intermediate Similarity	NPC212967
0.8393	Intermediate Similarity	NPC476930
0.8393	Intermediate Similarity	NPC272196
0.8393	Intermediate Similarity	NPC96342
0.8391	Intermediate Similarity	NPC111536
0.8391	Intermediate Similarity	NPC5029
0.8391	Intermediate Similarity	NPC76128
0.8391	Intermediate Similarity	NPC271385
0.8391	Intermediate Similarity	NPC30432
0.8383	Intermediate Similarity	NPC148938
0.8383	Intermediate Similarity	NPC149618
0.8383	Intermediate Similarity	NPC89625
0.8382	Intermediate Similarity	NPC20734
0.8373	Intermediate Similarity	NPC217447
0.8373	Intermediate Similarity	NPC5871
0.8372	Intermediate Similarity	NPC476056
0.8372	Intermediate Similarity	NPC477517
0.8372	Intermediate Similarity	NPC17274
0.8372	Intermediate Similarity	NPC120857
0.8372	Intermediate Similarity	NPC85047
0.8364	Intermediate Similarity	NPC325983
0.8364	Intermediate Similarity	NPC470107
0.8364	Intermediate Similarity	NPC202595
0.8363	Intermediate Similarity	NPC472581
0.8363	Intermediate Similarity	NPC476931
0.8362	Intermediate Similarity	NPC104682
0.8361	Intermediate Similarity	NPC470193
0.8361	Intermediate Similarity	NPC470194
0.8361	Intermediate Similarity	NPC470198
0.8361	Intermediate Similarity	NPC470196
0.8361	Intermediate Similarity	NPC470200
0.8361	Intermediate Similarity	NPC316274
0.8361	Intermediate Similarity	NPC470195
0.8361	Intermediate Similarity	NPC282474
0.8361	Intermediate Similarity	NPC470197
0.8354	Intermediate Similarity	NPC240253
0.8354	Intermediate Similarity	NPC256672
0.8354	Intermediate Similarity	NPC27221
0.8354	Intermediate Similarity	NPC471642
0.8354	Intermediate Similarity	NPC7025
0.8354	Intermediate Similarity	NPC240622
0.8354	Intermediate Similarity	NPC471641
0.8354	Intermediate Similarity	NPC39195
0.8353	Intermediate Similarity	NPC137232
0.8352	Intermediate Similarity	NPC324220
0.8352	Intermediate Similarity	NPC46958
0.8352	Intermediate Similarity	NPC475246
0.8352	Intermediate Similarity	NPC312630
0.8352	Intermediate Similarity	NPC470199
0.8352	Intermediate Similarity	NPC314459
0.8344	Intermediate Similarity	NPC290133
0.8344	Intermediate Similarity	NPC472033
0.8344	Intermediate Similarity	NPC24136
0.8344	Intermediate Similarity	NPC187282
0.8343	Intermediate Similarity	NPC277510
0.8343	Intermediate Similarity	NPC470336
0.8343	Intermediate Similarity	NPC30550
0.8343	Intermediate Similarity	NPC476349
0.8343	Intermediate Similarity	NPC314672
0.8343	Intermediate Similarity	NPC40583
0.8343	Intermediate Similarity	NPC229051
0.8343	Intermediate Similarity	NPC470333
0.8343	Intermediate Similarity	NPC470335
0.8343	Intermediate Similarity	NPC476350
0.8343	Intermediate Similarity	NPC131862
0.8343	Intermediate Similarity	NPC244750
0.8343	Intermediate Similarity	NPC295436
0.8343	Intermediate Similarity	NPC472617
0.8333	Intermediate Similarity	NPC28042
0.8333	Intermediate Similarity	NPC247677
0.8333	Intermediate Similarity	NPC160015
0.8324	Intermediate Similarity	NPC225419
0.8324	Intermediate Similarity	NPC472622
0.8323	Intermediate Similarity	NPC235333
0.8323	Intermediate Similarity	NPC1477
0.8323	Intermediate Similarity	NPC192189
0.8323	Intermediate Similarity	NPC329844
0.8323	Intermediate Similarity	NPC210942
0.8323	Intermediate Similarity	NPC213608
0.8323	Intermediate Similarity	NPC122365
0.8323	Intermediate Similarity	NPC169990
0.8315	Intermediate Similarity	NPC477860
0.8315	Intermediate Similarity	NPC315221
0.8315	Intermediate Similarity	NPC208069
0.8315	Intermediate Similarity	NPC475161
0.8314	Intermediate Similarity	NPC25361
0.8314	Intermediate Similarity	NPC189689
0.8313	Intermediate Similarity	NPC148945
0.8313	Intermediate Similarity	NPC478148
0.8313	Intermediate Similarity	NPC106372
0.8313	Intermediate Similarity	NPC58668
0.8313	Intermediate Similarity	NPC46882
0.8313	Intermediate Similarity	NPC78835
0.8313	Intermediate Similarity	NPC309512
0.8313	Intermediate Similarity	NPC204561
0.8313	Intermediate Similarity	NPC132990
0.8313	Intermediate Similarity	NPC316960
0.8313	Intermediate Similarity	NPC317715

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 NPC91650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	991
0.2-0.3	1880
0.3-0.4	2547
0.4-0.5	1848
0.5-0.6	996
0.6-0.7	403
0.7-0.8	140
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD6959	Discontinued
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8284	Intermediate Similarity	NPD7075	Discontinued
0.8274	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7411	Suspended
0.8103	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3749	Approved
0.8061	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6801	Discontinued
0.8034	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7473	Discontinued
0.7952	Intermediate Similarity	NPD2532	Approved
0.7952	Intermediate Similarity	NPD2533	Approved
0.7952	Intermediate Similarity	NPD2534	Approved
0.7914	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1549	Phase 2
0.7886	Intermediate Similarity	NPD6232	Discontinued
0.7874	Intermediate Similarity	NPD5494	Approved
0.787	Intermediate Similarity	NPD3226	Approved
0.7865	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD920	Approved
0.7853	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1247	Approved
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7824	Intermediate Similarity	NPD4380	Phase 2
0.7818	Intermediate Similarity	NPD3750	Approved
0.7816	Intermediate Similarity	NPD919	Approved
0.7816	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7768	Phase 2
0.7803	Intermediate Similarity	NPD3882	Suspended
0.7797	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6166	Phase 2
0.7797	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7759	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2800	Approved
0.7738	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7251	Discontinued
0.7733	Intermediate Similarity	NPD1934	Approved
0.7701	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7808	Phase 3
0.7688	Intermediate Similarity	NPD1465	Phase 2
0.7683	Intermediate Similarity	NPD2796	Approved
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1243	Approved
0.7644	Intermediate Similarity	NPD3817	Phase 2
0.7644	Intermediate Similarity	NPD5402	Approved
0.7636	Intermediate Similarity	NPD1471	Phase 3
0.7633	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7074	Phase 3
0.7622	Intermediate Similarity	NPD1510	Phase 2
0.7622	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD3751	Discontinued
0.7605	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7054	Approved
0.7558	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8312	Approved
0.7554	Intermediate Similarity	NPD8313	Approved
0.7544	Intermediate Similarity	NPD5403	Approved
0.7542	Intermediate Similarity	NPD3926	Phase 2
0.753	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD2344	Approved
0.7527	Intermediate Similarity	NPD7472	Approved
0.7515	Intermediate Similarity	NPD3748	Approved
0.7514	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.7486	Intermediate Similarity	NPD2801	Approved
0.7485	Intermediate Similarity	NPD1512	Approved
0.7485	Intermediate Similarity	NPD1240	Approved
0.747	Intermediate Similarity	NPD1551	Phase 2
0.7436	Intermediate Similarity	NPD7435	Discontinued
0.7427	Intermediate Similarity	NPD5401	Approved
0.7424	Intermediate Similarity	NPD8151	Discontinued
0.7418	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7371	Intermediate Similarity	NPD6782	Approved
0.7371	Intermediate Similarity	NPD6779	Approved
0.7371	Intermediate Similarity	NPD6778	Approved
0.7371	Intermediate Similarity	NPD6781	Approved
0.7371	Intermediate Similarity	NPD6777	Approved
0.7371	Intermediate Similarity	NPD6780	Approved
0.7371	Intermediate Similarity	NPD6776	Approved
0.7368	Intermediate Similarity	NPD7390	Discontinued
0.7368	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7365	Intermediate Similarity	NPD6099	Approved
0.7365	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD2309	Approved
0.7347	Intermediate Similarity	NPD7697	Approved
0.7347	Intermediate Similarity	NPD7696	Phase 3
0.7347	Intermediate Similarity	NPD7698	Approved
0.734	Intermediate Similarity	NPD8150	Discontinued
0.7326	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3787	Discontinued
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD7871	Phase 2
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7219	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7874	Approved
0.7214	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7701	Phase 2
0.7198	Intermediate Similarity	NPD7229	Phase 3
0.7194	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4628	Phase 3
0.7173	Intermediate Similarity	NPD4287	Approved
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.7158	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD37	Approved
0.7128	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6234	Discontinued
0.712	Intermediate Similarity	NPD2403	Approved
0.7113	Intermediate Similarity	NPD6534	Approved
0.7113	Intermediate Similarity	NPD6535	Approved
0.7111	Intermediate Similarity	NPD4965	Approved
0.7111	Intermediate Similarity	NPD4966	Approved
0.7111	Intermediate Similarity	NPD4967	Phase 2
0.7105	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6808	Phase 2
0.7094	Intermediate Similarity	NPD7801	Approved
0.7094	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7783	Phase 2
0.7093	Intermediate Similarity	NPD7003	Approved
0.7092	Intermediate Similarity	NPD7699	Phase 2
0.7092	Intermediate Similarity	NPD7700	Phase 2
0.7091	Intermediate Similarity	NPD4625	Phase 3
0.7086	Intermediate Similarity	NPD6273	Approved
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7062	Intermediate Similarity	NPD7458	Discontinued
0.7048	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD3268	Approved
0.7043	Intermediate Similarity	NPD7177	Discontinued
0.703	Intermediate Similarity	NPD4908	Phase 1
0.7026	Intermediate Similarity	NPD4360	Phase 2
0.7026	Intermediate Similarity	NPD4363	Phase 3
0.7024	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6983	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4288	Approved
0.6957	Remote Similarity	NPD7199	Phase 2
0.6952	Remote Similarity	NPD8366	Approved
0.6951	Remote Similarity	NPD1470	Approved
0.6946	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4749	Approved
0.6932	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD230	Phase 1
0.6901	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6764	Approved
0.6895	Remote Similarity	NPD6765	Approved
0.6887	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8285	Discontinued
0.6872	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2296	Approved
0.6866	Remote Similarity	NPD6823	Phase 2
0.6864	Remote Similarity	NPD943	Approved
0.6854	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1203	Approved
0.6845	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6832	Phase 2
0.6824	Remote Similarity	NPD6355	Discontinued
0.6822	Remote Similarity	NPD8491	Approved
0.6813	Remote Similarity	NPD8455	Phase 2
0.681	Remote Similarity	NPD1610	Phase 2
0.681	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2798	Approved
0.6806	Remote Similarity	NPD7240	Approved
0.6806	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7033	Discontinued
0.6796	Remote Similarity	NPD5890	Approved
0.6796	Remote Similarity	NPD5889	Approved
0.6792	Remote Similarity	NPD7907	Approved
0.6789	Remote Similarity	NPD1729	Discontinued
0.6788	Remote Similarity	NPD1283	Approved
0.6782	Remote Similarity	NPD3057	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