NPASS Compound

Structure

NPC50872 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 2.4899 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5890 7.3722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 2.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 4.1361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 3.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 4.9451 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 -1.5388 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 3.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1767 6.5632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.2361 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 -1.5388 3.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3578 4.8406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 4.2361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 3.9271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1713 6.6677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.7361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 5.6496 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 0.0000 5.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 26 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 27 1 0 0 0 0 20 30 2 0 0 0 0 20 33 1 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 1 0 0 0 24 15 1 6 0 0 0 24 34 1 0 0 0 0 25 29 1 6 0 0 0 25 33 1 0 0 0 0 26 29 1 1 0 0 0 26 35 1 0 0 0 0 27 31 2 0 0 0 0 27 34 1 0 0 0 0 28 32 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.24
Volume:	504.927
LogP:	6.02
LogD:	4.03
LogS:	-4.31
# Rotatable Bonds:	5
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	5.108
Fsp3:	0.448
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:	-4.873
MDCK Permeability:	1.8600865587359294e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	96.11811828613281%
Volume Distribution (VD):	2.16
Pgp-substrate:	5.589879512786865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.746
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.508
CYP2C9-substrate:	0.459
CYP2D6-inhibitor:	0.266
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	12.212
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.701
Human Hepatotoxicity (H-HT):	0.884
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.94
Carcinogencity:	0.515
Eye Corrosion:	0.015
Eye Irritation:	0.027
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC50872

Natural Product ID:	NPC50872
*Common Name:**	Malayenolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BYTXNCPKVDXTRC-DIAZDVSWSA-N
Standard InCHI:	InChI=1S/C29H34O6/c1-17-11-13-26(35-28(32)21-9-7-6-8-10-21)29(5)23(18(2)12-14-25(29)33-20(4)30)16-22-19(3)27(31)34-24(22)15-17/h6-10,12,15,23-26H,11,13-14,16H2,1-5H3/b17-15-/t23-,24-,25-,26-,29+/m0/s1
SMILES:	C/C/1=C/[C@H]2C(=C(C)C(=O)O2)C[C@H]2C(=CC[C@@H]([C@]2(C)[C@H](CC1)OC(=O)c1ccccc1)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455344
PubChem CID:	10696013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO26533	Veretillum malayense	Species	Veretillidae	Eukaryota	n.a.	indonesian sea	n.a.	PMID[10217714]
NPO26533	Veretillum malayense	Species	Veretillidae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LC50	=	100.0	ug.mL-1	PMID[479195]

☑ 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 NPC50872 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	246
0.1-0.2	1172
0.2-0.3	2374
0.3-0.4	6263
0.4-0.5	11839
0.5-0.6	13923
0.6-0.7	5920
0.7-0.8	888
0.8-0.85	63
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC476599
0.896	High Similarity	NPC238370
0.8908	High Similarity	NPC473243
0.885	High Similarity	NPC469636
0.8651	High Similarity	NPC147561
0.8632	High Similarity	NPC307651
0.8629	High Similarity	NPC275576
0.856	High Similarity	NPC169913
0.8547	High Similarity	NPC128368
0.8538	High Similarity	NPC472551
0.8538	High Similarity	NPC472545
0.8473	Intermediate Similarity	NPC39549
0.8462	Intermediate Similarity	NPC82899
0.8462	Intermediate Similarity	NPC473216
0.8462	Intermediate Similarity	NPC473399
0.8462	Intermediate Similarity	NPC270699
0.845	Intermediate Similarity	NPC472656
0.8438	Intermediate Similarity	NPC470278
0.8413	Intermediate Similarity	NPC473220
0.8413	Intermediate Similarity	NPC470753
0.8385	Intermediate Similarity	NPC203486
0.8385	Intermediate Similarity	NPC474608
0.8376	Intermediate Similarity	NPC474157
0.8376	Intermediate Similarity	NPC1082
0.8376	Intermediate Similarity	NPC305912
0.8372	Intermediate Similarity	NPC472394
0.8362	Intermediate Similarity	NPC83628
0.8362	Intermediate Similarity	NPC265407
0.8346	Intermediate Similarity	NPC472547
0.8333	Intermediate Similarity	NPC470765
0.8333	Intermediate Similarity	NPC149691
0.8321	Intermediate Similarity	NPC195647
0.8321	Intermediate Similarity	NPC17877
0.8321	Intermediate Similarity	NPC66761
0.8321	Intermediate Similarity	NPC291638
0.8321	Intermediate Similarity	NPC472577
0.8291	Intermediate Similarity	NPC214067
0.8291	Intermediate Similarity	NPC196246
0.8291	Intermediate Similarity	NPC251854
0.8291	Intermediate Similarity	NPC93084
0.8284	Intermediate Similarity	NPC224491
0.8268	Intermediate Similarity	NPC51292
0.825	Intermediate Similarity	NPC210092
0.8246	Intermediate Similarity	NPC474365
0.8246	Intermediate Similarity	NPC301943
0.8244	Intermediate Similarity	NPC126516
0.8244	Intermediate Similarity	NPC48929
0.8244	Intermediate Similarity	NPC329913
0.8222	Intermediate Similarity	NPC472546
0.822	Intermediate Similarity	NPC210089
0.8209	Intermediate Similarity	NPC183270
0.8209	Intermediate Similarity	NPC477904
0.8205	Intermediate Similarity	NPC474364
0.8205	Intermediate Similarity	NPC10251
0.8205	Intermediate Similarity	NPC17417
0.8195	Intermediate Similarity	NPC183122
0.8195	Intermediate Similarity	NPC475373
0.8195	Intermediate Similarity	NPC283375
0.8182	Intermediate Similarity	NPC226093
0.8154	Intermediate Similarity	NPC72915
0.8145	Intermediate Similarity	NPC238861
0.8145	Intermediate Similarity	NPC77000
0.8142	Intermediate Similarity	NPC146351
0.8134	Intermediate Similarity	NPC475652
0.8134	Intermediate Similarity	NPC210591
0.8134	Intermediate Similarity	NPC214550
0.812	Intermediate Similarity	NPC472374
0.812	Intermediate Similarity	NPC56493
0.812	Intermediate Similarity	NPC472372
0.811	Intermediate Similarity	NPC295664
0.8106	Intermediate Similarity	NPC324898
0.8106	Intermediate Similarity	NPC134937
0.8106	Intermediate Similarity	NPC298547
0.8099	Intermediate Similarity	NPC474095
0.8095	Intermediate Similarity	NPC472703
0.8077	Intermediate Similarity	NPC475508
0.8077	Intermediate Similarity	NPC42234
0.8077	Intermediate Similarity	NPC473247
0.8074	Intermediate Similarity	NPC476094
0.8074	Intermediate Similarity	NPC90614
0.8074	Intermediate Similarity	NPC4341
0.8074	Intermediate Similarity	NPC473060
0.8074	Intermediate Similarity	NPC43241
0.8074	Intermediate Similarity	NPC275592
0.8074	Intermediate Similarity	NPC473758
0.8074	Intermediate Similarity	NPC48017
0.8074	Intermediate Similarity	NPC211137
0.8074	Intermediate Similarity	NPC147880
0.8074	Intermediate Similarity	NPC171207
0.8074	Intermediate Similarity	NPC184747
0.8074	Intermediate Similarity	NPC473109
0.8074	Intermediate Similarity	NPC475400
0.8074	Intermediate Similarity	NPC200592
0.8074	Intermediate Similarity	NPC473081
0.8074	Intermediate Similarity	NPC473613
0.8074	Intermediate Similarity	NPC473085
0.8074	Intermediate Similarity	NPC97667
0.8074	Intermediate Similarity	NPC473112
0.8074	Intermediate Similarity	NPC100913
0.8065	Intermediate Similarity	NPC204784
0.8053	Intermediate Similarity	NPC35448
0.8053	Intermediate Similarity	NPC78701
0.8053	Intermediate Similarity	NPC225060
0.8045	Intermediate Similarity	NPC279637
0.8045	Intermediate Similarity	NPC477893
0.8045	Intermediate Similarity	NPC477896
0.8045	Intermediate Similarity	NPC149401
0.8034	Intermediate Similarity	NPC119271
0.8031	Intermediate Similarity	NPC51079
0.8031	Intermediate Similarity	NPC472704
0.8029	Intermediate Similarity	NPC91703
0.8017	Intermediate Similarity	NPC308744
0.8017	Intermediate Similarity	NPC477411
0.8017	Intermediate Similarity	NPC153053
0.8015	Intermediate Similarity	NPC16912
0.8015	Intermediate Similarity	NPC87448
0.8015	Intermediate Similarity	NPC472576
0.8015	Intermediate Similarity	NPC118080
0.8015	Intermediate Similarity	NPC291599
0.8015	Intermediate Similarity	NPC27377
0.8015	Intermediate Similarity	NPC97947
0.8015	Intermediate Similarity	NPC41481
0.8	Intermediate Similarity	NPC472371
0.8	Intermediate Similarity	NPC9905
0.8	Intermediate Similarity	NPC472395
0.7984	Intermediate Similarity	NPC472706
0.7983	Intermediate Similarity	NPC174099
0.7982	Intermediate Similarity	NPC325497
0.797	Intermediate Similarity	NPC153617
0.7965	Intermediate Similarity	NPC249912
0.7965	Intermediate Similarity	NPC92754
0.7965	Intermediate Similarity	NPC276775
0.7956	Intermediate Similarity	NPC192658
0.7956	Intermediate Similarity	NPC34012
0.7955	Intermediate Similarity	NPC239358
0.7955	Intermediate Similarity	NPC477360
0.7955	Intermediate Similarity	NPC233692
0.7955	Intermediate Similarity	NPC233860
0.7949	Intermediate Similarity	NPC269457
0.7949	Intermediate Similarity	NPC209632
0.7941	Intermediate Similarity	NPC162613
0.7941	Intermediate Similarity	NPC87934
0.7939	Intermediate Similarity	NPC471832
0.7939	Intermediate Similarity	NPC272946
0.7937	Intermediate Similarity	NPC144547
0.7934	Intermediate Similarity	NPC272524
0.7934	Intermediate Similarity	NPC474176
0.7931	Intermediate Similarity	NPC89886
0.7926	Intermediate Similarity	NPC327511
0.7926	Intermediate Similarity	NPC205305
0.7923	Intermediate Similarity	NPC472707
0.7917	Intermediate Similarity	NPC167504
0.7914	Intermediate Similarity	NPC472556
0.7913	Intermediate Similarity	NPC42211
0.7913	Intermediate Similarity	NPC70624
0.7907	Intermediate Similarity	NPC137416
0.7907	Intermediate Similarity	NPC121272
0.7903	Intermediate Similarity	NPC152812
0.7903	Intermediate Similarity	NPC45794
0.7899	Intermediate Similarity	NPC191387
0.7899	Intermediate Similarity	NPC475429
0.7899	Intermediate Similarity	NPC270498
0.7899	Intermediate Similarity	NPC147217
0.7899	Intermediate Similarity	NPC473673
0.7899	Intermediate Similarity	NPC191082
0.7899	Intermediate Similarity	NPC477468
0.7899	Intermediate Similarity	NPC163087
0.7899	Intermediate Similarity	NPC131966
0.7899	Intermediate Similarity	NPC177340
0.7899	Intermediate Similarity	NPC246480
0.7899	Intermediate Similarity	NPC139067
0.7895	Intermediate Similarity	NPC472248
0.7883	Intermediate Similarity	NPC266374
0.7881	Intermediate Similarity	NPC37622
0.7881	Intermediate Similarity	NPC30594
0.7869	Intermediate Similarity	NPC196075
0.7868	Intermediate Similarity	NPC121268
0.7868	Intermediate Similarity	NPC53361
0.7863	Intermediate Similarity	NPC114594
0.7863	Intermediate Similarity	NPC31786
0.7857	Intermediate Similarity	NPC474935
0.7857	Intermediate Similarity	NPC988
0.7857	Intermediate Similarity	NPC289432
0.7852	Intermediate Similarity	NPC477358
0.7851	Intermediate Similarity	NPC79496
0.7851	Intermediate Similarity	NPC321852
0.7842	Intermediate Similarity	NPC475122
0.7842	Intermediate Similarity	NPC472573
0.7842	Intermediate Similarity	NPC25768
0.7842	Intermediate Similarity	NPC241951
0.7842	Intermediate Similarity	NPC11685
0.7842	Intermediate Similarity	NPC95810
0.7842	Intermediate Similarity	NPC475759
0.7842	Intermediate Similarity	NPC125106
0.7842	Intermediate Similarity	NPC51314
0.7842	Intermediate Similarity	NPC67777
0.7842	Intermediate Similarity	NPC95265
0.7842	Intermediate Similarity	NPC163719
0.7842	Intermediate Similarity	NPC476974
0.7842	Intermediate Similarity	NPC38696

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 NPC50872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	853
0.2-0.3	1243
0.3-0.4	2676
0.4-0.5	2461
0.5-0.6	1295
0.6-0.7	364
0.7-0.8	38
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8534	High Similarity	NPD2181	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2182	Approved
0.8145	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7236	Approved
0.7863	Intermediate Similarity	NPD164	Approved
0.7826	Intermediate Similarity	NPD1238	Approved
0.7734	Intermediate Similarity	NPD6287	Discontinued
0.7669	Intermediate Similarity	NPD7008	Discontinued
0.7656	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7094	Approved
0.7642	Intermediate Similarity	NPD6858	Approved
0.7639	Intermediate Similarity	NPD7239	Suspended
0.7541	Intermediate Similarity	NPD2067	Discontinued
0.752	Intermediate Similarity	NPD2629	Approved
0.752	Intermediate Similarity	NPD5951	Approved
0.7444	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1930	Approved
0.7333	Intermediate Similarity	NPD1929	Approved
0.7333	Intermediate Similarity	NPD6647	Phase 2
0.7333	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6273	Approved
0.7241	Intermediate Similarity	NPD1202	Approved
0.7214	Intermediate Similarity	NPD2567	Approved
0.7214	Intermediate Similarity	NPD2569	Approved
0.7206	Intermediate Similarity	NPD6832	Phase 2
0.72	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4198	Discontinued
0.7183	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7057	Phase 3
0.7171	Intermediate Similarity	NPD7058	Phase 2
0.7164	Intermediate Similarity	NPD1876	Approved
0.7153	Intermediate Similarity	NPD8166	Discontinued
0.7153	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD3972	Approved
0.7131	Intermediate Similarity	NPD5909	Discontinued
0.7119	Intermediate Similarity	NPD1989	Approved
0.7101	Intermediate Similarity	NPD3764	Approved
0.7094	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2066	Phase 3
0.708	Intermediate Similarity	NPD9259	Approved
0.708	Intermediate Similarity	NPD9257	Approved
0.7059	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6085	Phase 2
0.705	Intermediate Similarity	NPD8032	Phase 2
0.705	Intermediate Similarity	NPD7961	Discontinued
0.705	Intermediate Similarity	NPD6663	Approved
0.705	Intermediate Similarity	NPD7713	Phase 3
0.7042	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD2198	Approved
0.7037	Intermediate Similarity	NPD2199	Approved
0.7034	Intermediate Similarity	NPD7003	Approved
0.7031	Intermediate Similarity	NPD1241	Discontinued
0.7031	Intermediate Similarity	NPD6010	Discontinued
0.7023	Intermediate Similarity	NPD9545	Approved
0.7023	Intermediate Similarity	NPD7741	Discontinued
0.7015	Intermediate Similarity	NPD6637	Approved
0.7009	Intermediate Similarity	NPD7631	Approved
0.7007	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6993	Remote Similarity	NPD2438	Suspended
0.6992	Remote Similarity	NPD1237	Approved
0.6983	Remote Similarity	NPD3672	Approved
0.6983	Remote Similarity	NPD3673	Approved
0.6977	Remote Similarity	NPD4766	Approved
0.695	Remote Similarity	NPD6355	Discontinued
0.6944	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7798	Approved
0.694	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD7609	Phase 3
0.6923	Remote Similarity	NPD3748	Approved
0.6917	Remote Similarity	NPD3495	Discontinued
0.6906	Remote Similarity	NPD6039	Approved
0.6887	Remote Similarity	NPD7458	Discontinued
0.688	Remote Similarity	NPD3134	Approved
0.688	Remote Similarity	NPD6685	Approved
0.6875	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD7799	Discontinued
0.687	Remote Similarity	NPD9493	Approved
0.687	Remote Similarity	NPD1087	Approved
0.6864	Remote Similarity	NPD1088	Approved
0.6842	Remote Similarity	NPD5585	Approved
0.6842	Remote Similarity	NPD5691	Approved
0.6838	Remote Similarity	NPD9258	Approved
0.6838	Remote Similarity	NPD9256	Approved
0.6835	Remote Similarity	NPD7055	Discontinued
0.6818	Remote Similarity	NPD7610	Discontinued
0.6818	Remote Similarity	NPD2347	Approved
0.6812	Remote Similarity	NPD2798	Approved
0.6806	Remote Similarity	NPD7305	Phase 1
0.6803	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1283	Approved
0.6788	Remote Similarity	NPD5667	Approved
0.6783	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4307	Phase 2
0.6761	Remote Similarity	NPD3373	Approved
0.6761	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2531	Phase 2
0.675	Remote Similarity	NPD1693	Approved
0.6739	Remote Similarity	NPD3267	Approved
0.6739	Remote Similarity	NPD3266	Approved
0.6739	Remote Similarity	NPD2797	Approved
0.6738	Remote Similarity	NPD2313	Discontinued
0.6735	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1282	Approved
0.6721	Remote Similarity	NPD9495	Approved
0.6721	Remote Similarity	NPD5926	Approved
0.6719	Remote Similarity	NPD5240	Approved
0.6719	Remote Similarity	NPD4233	Approved
0.6719	Remote Similarity	NPD4234	Approved
0.6719	Remote Similarity	NPD5239	Approved
0.6719	Remote Similarity	NPD5237	Approved
0.6719	Remote Similarity	NPD5236	Approved
0.6719	Remote Similarity	NPD5235	Approved
0.6716	Remote Similarity	NPD3024	Approved
0.6716	Remote Similarity	NPD3025	Approved
0.6713	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2346	Discontinued
0.671	Remote Similarity	NPD7819	Suspended
0.6695	Remote Similarity	NPD1086	Approved
0.6695	Remote Similarity	NPD1090	Approved
0.6695	Remote Similarity	NPD1089	Approved
0.6694	Remote Similarity	NPD1932	Approved
0.6693	Remote Similarity	NPD1358	Approved
0.6692	Remote Similarity	NPD6065	Approved
0.6692	Remote Similarity	NPD2607	Approved
0.6691	Remote Similarity	NPD4807	Approved
0.6691	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4806	Approved
0.6691	Remote Similarity	NPD1019	Discontinued
0.6689	Remote Similarity	NPD4110	Phase 3
0.6689	Remote Similarity	NPD3750	Approved
0.6689	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD5306	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD2201	Approved
0.6644	Remote Similarity	NPD2796	Approved
0.6644	Remote Similarity	NPD3887	Approved
0.6643	Remote Similarity	NPD4140	Approved
0.6642	Remote Similarity	NPD7009	Phase 2
0.6642	Remote Similarity	NPD9717	Approved
0.6641	Remote Similarity	NPD2652	Approved
0.6641	Remote Similarity	NPD2650	Approved
0.6641	Remote Similarity	NPD2329	Discontinued
0.664	Remote Similarity	NPD5765	Approved
0.6623	Remote Similarity	NPD6599	Discontinued
0.662	Remote Similarity	NPD3268	Approved
0.6618	Remote Similarity	NPD3026	Approved
0.6618	Remote Similarity	NPD3023	Approved
0.6615	Remote Similarity	NPD969	Suspended
0.6612	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD9260	Approved
0.661	Remote Similarity	NPD800	Approved
0.6606	Remote Similarity	NPD8368	Discontinued
0.6603	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6005	Phase 3
0.6599	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6004	Phase 3
0.6599	Remote Similarity	NPD6002	Phase 3
0.6594	Remote Similarity	NPD5327	Phase 3
0.6594	Remote Similarity	NPD4359	Approved
0.6593	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1651	Approved
0.6589	Remote Similarity	NPD1752	Approved
0.6589	Remote Similarity	NPD1756	Approved
0.6589	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8407	Phase 2
0.6581	Remote Similarity	NPD650	Approved
0.6579	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4308	Phase 3
0.6573	Remote Similarity	NPD7714	Approved
0.6573	Remote Similarity	NPD7715	Approved
0.6562	Remote Similarity	NPD8127	Discontinued
0.6554	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD3019	Approved
0.6544	Remote Similarity	NPD5126	Approved
0.6544	Remote Similarity	NPD4626	Approved
0.6544	Remote Similarity	NPD5125	Phase 3
0.6535	Remote Similarity	NPD5048	Discontinued
0.6531	Remote Similarity	NPD4476	Approved
0.6531	Remote Similarity	NPD4477	Approved
0.6529	Remote Similarity	NPD1563	Approved
0.6522	Remote Similarity	NPD1608	Approved
0.6519	Remote Similarity	NPD1894	Discontinued
0.6519	Remote Similarity	NPD7768	Phase 2
0.6513	Remote Similarity	NPD2533	Approved
0.6513	Remote Similarity	NPD2534	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