NPASS Compound

Structure

NPC26532 OpenBabel07101718322D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 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 -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 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 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 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 3.5116 1.0933 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 0.8660 -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 1 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 -0.8660 -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 1 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 -0.0000 0.0000 C 0 0 1 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 21 2 0 0 0 0 12 13 2 0 0 0 0 12 24 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 20 1 1 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	348.149
LogP:	3.263
LogD:	3.082
LogS:	-4.198
# Rotatable Bonds:	3
TPSA:	64.35
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	4.652
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	3.400025889277458e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.89
Plasma Protein Binding (PPB):	82.21927642822266%
Volume Distribution (VD):	1.182
Pgp-substrate:	8.387439727783203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.271
CYP2C19-substrate:	0.377
CYP2C9-inhibitor:	0.467
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	9.976
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.247
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.683
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.365
Carcinogencity:	0.714
Eye Corrosion:	0.015
Eye Irritation:	0.058
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC26532

Natural Product ID:	NPC26532
*Common Name:**	KUZVESKWERRMKK-PIOJPPRKSA-N
IUPAC Name:	n.a.
Synonyms:	7-Hydroxy Hydichinal
Standard InCHIKey:	KUZVESKWERRMKK-PIOJPPRKSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-19(2)8-4-9-20(3)15(6-5-13-7-10-24-12-13)14(11-21)16(22)17(23)18(19)20/h5-7,10-12,15,18,22H,4,8-9H2,1-3H3/b6-5+/t15-,18-,20+/m0/s1
SMILES:	O=CC1=C(O)C(=O)[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL582854
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	23360.0	nM	PMID[471358]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	15950.0	nM	PMID[471358]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	21580.0	nM	PMID[471358]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	37850.0	nM	PMID[471358]

☑ 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 NPC26532 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	230
0.1-0.2	1272
0.2-0.3	2838
0.3-0.4	6597
0.4-0.5	12389
0.5-0.6	11271
0.6-0.7	7384
0.7-0.8	626
0.8-0.85	51
0.85-0.9	30
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC246392
0.959	High Similarity	NPC290955
0.9435	High Similarity	NPC208389
0.9355	High Similarity	NPC279877
0.9167	High Similarity	NPC87466
0.8889	High Similarity	NPC23086
0.881	High Similarity	NPC300098
0.881	High Similarity	NPC290193
0.8769	High Similarity	NPC473982
0.875	High Similarity	NPC207294
0.875	High Similarity	NPC112706
0.8692	High Similarity	NPC61788
0.8682	High Similarity	NPC59502
0.8672	High Similarity	NPC83178
0.8605	High Similarity	NPC477966
0.8605	High Similarity	NPC329707
0.8605	High Similarity	NPC477123
0.8594	High Similarity	NPC46536
0.8594	High Similarity	NPC138139
0.8593	High Similarity	NPC202260
0.8571	High Similarity	NPC477967
0.8571	High Similarity	NPC158525
0.8561	High Similarity	NPC218838
0.8548	High Similarity	NPC243704
0.8529	High Similarity	NPC148374
0.8529	High Similarity	NPC90296
0.8516	High Similarity	NPC471074
0.8516	High Similarity	NPC473885
0.8492	Intermediate Similarity	NPC97566
0.8485	Intermediate Similarity	NPC471995
0.8462	Intermediate Similarity	NPC477039
0.8462	Intermediate Similarity	NPC477040
0.8456	Intermediate Similarity	NPC474722
0.8438	Intermediate Similarity	NPC118853
0.843	Intermediate Similarity	NPC277525
0.8409	Intermediate Similarity	NPC89133
0.8406	Intermediate Similarity	NPC263337
0.8372	Intermediate Similarity	NPC179354
0.837	Intermediate Similarity	NPC46896
0.8359	Intermediate Similarity	NPC16922
0.8345	Intermediate Similarity	NPC243577
0.8333	Intermediate Similarity	NPC476925
0.8333	Intermediate Similarity	NPC246164
0.8321	Intermediate Similarity	NPC476917
0.8321	Intermediate Similarity	NPC327527
0.8321	Intermediate Similarity	NPC90953
0.8309	Intermediate Similarity	NPC307401
0.8306	Intermediate Similarity	NPC150895
0.8296	Intermediate Similarity	NPC476947
0.8295	Intermediate Similarity	NPC477038
0.8295	Intermediate Similarity	NPC477965
0.8284	Intermediate Similarity	NPC471006
0.8284	Intermediate Similarity	NPC470740
0.8281	Intermediate Similarity	NPC317217
0.8261	Intermediate Similarity	NPC201370
0.8261	Intermediate Similarity	NPC473983
0.8248	Intermediate Similarity	NPC472376
0.8235	Intermediate Similarity	NPC146872
0.8217	Intermediate Similarity	NPC272899
0.8209	Intermediate Similarity	NPC471817
0.8175	Intermediate Similarity	NPC215109
0.8175	Intermediate Similarity	NPC170604
0.8168	Intermediate Similarity	NPC74612
0.8154	Intermediate Similarity	NPC178382
0.8154	Intermediate Similarity	NPC130275
0.8154	Intermediate Similarity	NPC243269
0.8143	Intermediate Similarity	NPC473152
0.8143	Intermediate Similarity	NPC52412
0.8134	Intermediate Similarity	NPC298190
0.8129	Intermediate Similarity	NPC67003
0.8116	Intermediate Similarity	NPC471996
0.8099	Intermediate Similarity	NPC185456
0.8092	Intermediate Similarity	NPC303010
0.8092	Intermediate Similarity	NPC474829
0.8085	Intermediate Similarity	NPC267632
0.8069	Intermediate Similarity	NPC228842
0.8069	Intermediate Similarity	NPC212257
0.8056	Intermediate Similarity	NPC93666
0.8043	Intermediate Similarity	NPC310830
0.8031	Intermediate Similarity	NPC312525
0.8031	Intermediate Similarity	NPC212918
0.8031	Intermediate Similarity	NPC217180
0.8029	Intermediate Similarity	NPC92941
0.8016	Intermediate Similarity	NPC205523
0.8015	Intermediate Similarity	NPC293253
0.8015	Intermediate Similarity	NPC65735
0.8015	Intermediate Similarity	NPC188377
0.8014	Intermediate Similarity	NPC272590
0.8014	Intermediate Similarity	NPC475519
0.8014	Intermediate Similarity	NPC121158
0.8	Intermediate Similarity	NPC56197
0.7986	Intermediate Similarity	NPC220094
0.7986	Intermediate Similarity	NPC236532
0.7986	Intermediate Similarity	NPC471174
0.7986	Intermediate Similarity	NPC476943
0.7986	Intermediate Similarity	NPC302987
0.7985	Intermediate Similarity	NPC120836
0.7985	Intermediate Similarity	NPC223063
0.7972	Intermediate Similarity	NPC245522
0.7972	Intermediate Similarity	NPC114513
0.797	Intermediate Similarity	NPC474830
0.7959	Intermediate Similarity	NPC294511
0.7959	Intermediate Similarity	NPC121615
0.7958	Intermediate Similarity	NPC476946
0.7943	Intermediate Similarity	NPC205765
0.7933	Intermediate Similarity	NPC472823
0.7917	Intermediate Similarity	NPC346
0.7914	Intermediate Similarity	NPC470742
0.7914	Intermediate Similarity	NPC42400
0.7902	Intermediate Similarity	NPC476944
0.7902	Intermediate Similarity	NPC251865
0.7891	Intermediate Similarity	NPC208906
0.7891	Intermediate Similarity	NPC144745
0.7877	Intermediate Similarity	NPC470998
0.7877	Intermediate Similarity	NPC234494
0.7868	Intermediate Similarity	NPC477645
0.7863	Intermediate Similarity	NPC36255
0.7862	Intermediate Similarity	NPC250228
0.7862	Intermediate Similarity	NPC216755
0.7862	Intermediate Similarity	NPC71821
0.7857	Intermediate Similarity	NPC177262
0.7852	Intermediate Similarity	NPC88958
0.7852	Intermediate Similarity	NPC281258
0.7847	Intermediate Similarity	NPC247221
0.7847	Intermediate Similarity	NPC56731
0.7847	Intermediate Similarity	NPC5676
0.7826	Intermediate Similarity	NPC106247
0.7823	Intermediate Similarity	NPC196846
0.7823	Intermediate Similarity	NPC470997
0.782	Intermediate Similarity	NPC230979
0.7815	Intermediate Similarity	NPC116639
0.7812	Intermediate Similarity	NPC79202
0.7812	Intermediate Similarity	NPC59035
0.7808	Intermediate Similarity	NPC476942
0.7808	Intermediate Similarity	NPC476941
0.78	Intermediate Similarity	NPC41880
0.78	Intermediate Similarity	NPC104736
0.7793	Intermediate Similarity	NPC478166
0.7793	Intermediate Similarity	NPC262198
0.7793	Intermediate Similarity	NPC233763
0.7786	Intermediate Similarity	NPC278832
0.7786	Intermediate Similarity	NPC64157
0.7786	Intermediate Similarity	NPC473268
0.7785	Intermediate Similarity	NPC282793
0.7785	Intermediate Similarity	NPC44606
0.7778	Intermediate Similarity	NPC238843
0.7778	Intermediate Similarity	NPC474279
0.7778	Intermediate Similarity	NPC142113
0.7778	Intermediate Similarity	NPC199044
0.7778	Intermediate Similarity	NPC474438
0.777	Intermediate Similarity	NPC472787
0.777	Intermediate Similarity	NPC209858
0.777	Intermediate Similarity	NPC265793
0.7769	Intermediate Similarity	NPC473969
0.7769	Intermediate Similarity	NPC137710
0.7761	Intermediate Similarity	NPC474260
0.7761	Intermediate Similarity	NPC81912
0.7761	Intermediate Similarity	NPC329694
0.7761	Intermediate Similarity	NPC329922
0.7755	Intermediate Similarity	NPC211625
0.7754	Intermediate Similarity	NPC474407
0.7754	Intermediate Similarity	NPC474426
0.7754	Intermediate Similarity	NPC474425
0.7748	Intermediate Similarity	NPC304692
0.7748	Intermediate Similarity	NPC194499
0.7748	Intermediate Similarity	NPC195954
0.7748	Intermediate Similarity	NPC88007
0.7748	Intermediate Similarity	NPC7059
0.7746	Intermediate Similarity	NPC61157
0.7746	Intermediate Similarity	NPC218204
0.7746	Intermediate Similarity	NPC473681
0.7746	Intermediate Similarity	NPC18904
0.7744	Intermediate Similarity	NPC83115
0.774	Intermediate Similarity	NPC476937
0.774	Intermediate Similarity	NPC255414
0.774	Intermediate Similarity	NPC476938
0.7734	Intermediate Similarity	NPC28054
0.7733	Intermediate Similarity	NPC469966
0.7733	Intermediate Similarity	NPC75310
0.7733	Intermediate Similarity	NPC214541
0.7733	Intermediate Similarity	NPC44675
0.773	Intermediate Similarity	NPC130976
0.7727	Intermediate Similarity	NPC471549
0.7727	Intermediate Similarity	NPC473379
0.7727	Intermediate Similarity	NPC261184
0.7724	Intermediate Similarity	NPC290038
0.7721	Intermediate Similarity	NPC198904
0.7718	Intermediate Similarity	NPC470996
0.7718	Intermediate Similarity	NPC44577
0.7718	Intermediate Similarity	NPC33938
0.7718	Intermediate Similarity	NPC145830
0.7704	Intermediate Similarity	NPC476016
0.7703	Intermediate Similarity	NPC46551
0.7698	Intermediate Similarity	NPC471998
0.7697	Intermediate Similarity	NPC474611
0.7697	Intermediate Similarity	NPC477403
0.7692	Intermediate Similarity	NPC21831
0.7692	Intermediate Similarity	NPC187547
0.7687	Intermediate Similarity	NPC478163
0.7687	Intermediate Similarity	NPC471007

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 NPC26532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	955
0.2-0.3	1743
0.3-0.4	2678
0.4-0.5	2118
0.5-0.6	1164
0.6-0.7	251
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7801	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1471	Phase 3
0.7386	Intermediate Similarity	NPD5761	Phase 2
0.7386	Intermediate Similarity	NPD5760	Phase 2
0.7383	Intermediate Similarity	NPD6273	Approved
0.7346	Intermediate Similarity	NPD6764	Approved
0.7346	Intermediate Similarity	NPD6765	Approved
0.7308	Intermediate Similarity	NPD1241	Discontinued
0.7292	Intermediate Similarity	NPD2799	Discontinued
0.7279	Intermediate Similarity	NPD3972	Approved
0.7279	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD8434	Phase 2
0.7192	Intermediate Similarity	NPD2344	Approved
0.7185	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1876	Approved
0.7169	Intermediate Similarity	NPD6785	Approved
0.7169	Intermediate Similarity	NPD6784	Approved
0.7115	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.7075	Intermediate Similarity	NPD2346	Discontinued
0.7071	Intermediate Similarity	NPD2798	Approved
0.7047	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.6981	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6599	Discontinued
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8032	Phase 2
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7458	Discontinued
0.6879	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD3268	Approved
0.6863	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6832	Phase 2
0.6824	Remote Similarity	NPD4308	Phase 3
0.6821	Remote Similarity	NPD4110	Phase 3
0.6821	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3750	Approved
0.6809	Remote Similarity	NPD1283	Approved
0.6786	Remote Similarity	NPD1608	Approved
0.6786	Remote Similarity	NPD9717	Approved
0.6781	Remote Similarity	NPD4140	Approved
0.6779	Remote Similarity	NPD1551	Phase 2
0.6774	Remote Similarity	NPD920	Approved
0.6759	Remote Similarity	NPD6798	Discontinued
0.6755	Remote Similarity	NPD2800	Approved
0.6752	Remote Similarity	NPD7028	Phase 2
0.6739	Remote Similarity	NPD5585	Approved
0.6739	Remote Similarity	NPD1651	Approved
0.6732	Remote Similarity	NPD7236	Approved
0.6732	Remote Similarity	NPD643	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7819	Suspended
0.6711	Remote Similarity	NPD8166	Discontinued
0.6711	Remote Similarity	NPD3748	Approved
0.6692	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7157	Approved
0.6691	Remote Similarity	NPD2932	Approved
0.6691	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD4534	Discontinued
0.6688	Remote Similarity	NPD6799	Approved
0.6688	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD3869	Phase 3
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD2354	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD3882	Suspended
0.6645	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3764	Approved
0.6643	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6643	Remote Similarity	NPD1203	Approved
0.6642	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6559	Discontinued
0.6623	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6002	Phase 3
0.6623	Remote Similarity	NPD5762	Approved
0.6623	Remote Similarity	NPD5763	Approved
0.6623	Remote Similarity	NPD6005	Phase 3
0.6623	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6004	Phase 3
0.662	Remote Similarity	NPD5327	Phase 3
0.6605	Remote Similarity	NPD7075	Discontinued
0.6603	Remote Similarity	NPD5049	Phase 3
0.6599	Remote Similarity	NPD6233	Phase 2
0.6599	Remote Similarity	NPD4062	Phase 3
0.6597	Remote Similarity	NPD5647	Approved
0.6596	Remote Similarity	NPD1281	Approved
0.6594	Remote Similarity	NPD9092	Discovery
0.6585	Remote Similarity	NPD8127	Discontinued
0.6585	Remote Similarity	NPD1247	Approved
0.6584	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1549	Phase 2
0.6579	Remote Similarity	NPD5958	Discontinued
0.6571	Remote Similarity	NPD3019	Approved
0.6571	Remote Similarity	NPD17	Approved
0.6562	Remote Similarity	NPD6279	Approved
0.6562	Remote Similarity	NPD6280	Approved
0.6552	Remote Similarity	NPD9494	Approved
0.6547	Remote Similarity	NPD1894	Discontinued
0.6541	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1243	Approved
0.6531	Remote Similarity	NPD411	Approved
0.6525	Remote Similarity	NPD3496	Discontinued
0.6519	Remote Similarity	NPD7239	Suspended
0.6513	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2353	Approved
0.6513	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5735	Approved
0.651	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2614	Approved
0.6503	Remote Similarity	NPD3749	Approved
0.6503	Remote Similarity	NPD4359	Approved
0.65	Remote Similarity	NPD7411	Suspended
0.65	Remote Similarity	NPD5691	Approved
0.6496	Remote Similarity	NPD690	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1510	Phase 2
0.6483	Remote Similarity	NPD1019	Discontinued
0.6481	Remote Similarity	NPD2296	Approved
0.6478	Remote Similarity	NPD2649	Approved
0.6478	Remote Similarity	NPD2651	Approved
0.6471	Remote Similarity	NPD2424	Discontinued
0.6467	Remote Similarity	NPD1607	Approved
0.6467	Remote Similarity	NPD6353	Approved
0.6463	Remote Similarity	NPD7008	Discontinued
0.646	Remote Similarity	NPD7577	Discontinued
0.646	Remote Similarity	NPD6801	Discontinued
0.6456	Remote Similarity	NPD5403	Approved
0.6454	Remote Similarity	NPD4626	Approved
0.6447	Remote Similarity	NPD2531	Phase 2
0.6447	Remote Similarity	NPD2438	Suspended
0.6444	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1240	Approved
0.6442	Remote Similarity	NPD7768	Phase 2
0.6433	Remote Similarity	NPD4661	Approved
0.6433	Remote Similarity	NPD4662	Approved
0.6433	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2533	Approved
0.6433	Remote Similarity	NPD2532	Approved
0.6433	Remote Similarity	NPD2534	Approved
0.6433	Remote Similarity	NPD5401	Approved
0.6429	Remote Similarity	NPD9545	Approved
0.6429	Remote Similarity	NPD3057	Approved
0.6424	Remote Similarity	NPD5494	Approved
0.642	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2182	Approved
0.6418	Remote Similarity	NPD2684	Approved
0.6414	Remote Similarity	NPD6362	Approved
0.641	Remote Similarity	NPD7440	Discontinued
0.6408	Remote Similarity	NPD3023	Approved
0.6408	Remote Similarity	NPD3026	Approved
0.6407	Remote Similarity	NPD3926	Phase 2
0.64	Remote Similarity	NPD447	Suspended
0.6391	Remote Similarity	NPD3134	Approved
0.6391	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3024	Approved
0.6383	Remote Similarity	NPD3025	Approved
0.6383	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD5951	Approved
0.6377	Remote Similarity	NPD2629	Approved
0.6376	Remote Similarity	NPD6663	Approved
0.637	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.637	Remote Similarity	NPD4624	Approved
0.637	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6287	Discontinued
0.6364	Remote Similarity	NPD1237	Approved
0.6364	Remote Similarity	NPD2897	Discontinued
0.6358	Remote Similarity	NPD6844	Discontinued
0.6358	Remote Similarity	NPD6653	Approved
0.6358	Remote Similarity	NPD6651	Approved
0.635	Remote Similarity	NPD7843	Approved
0.6347	Remote Similarity	NPD6808	Phase 2
0.6345	Remote Similarity	NPD8651	Approved
0.6345	Remote Similarity	NPD6696	Suspended
0.6341	Remote Similarity	NPD4947	Clinical (unspecified phase)

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