NPASS Compound

Structure

NPC238370 OpenBabel07101718202D 36 40 0 0 1 0 0 0 0 0999 V2000 6.0178 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9890 -2.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9389 4.0451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6814 -0.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9920 0.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1260 0.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9920 1.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2599 0.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1260 2.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4789 0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4789 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 -1.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -2.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3511 3.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2599 1.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5279 -2.3271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9890 -0.2091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5279 0.9090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1701 1.5135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5768 -3.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3939 2.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 0.6000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3566 3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2678 -4.5872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3939 3.4090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7579 2.3225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5279 -3.3271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5279 1.9090 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 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 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 19 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 15 25 1 0 0 0 0 17 20 2 0 0 0 0 17 26 1 0 0 0 0 18 30 2 0 0 0 0 18 33 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 21 13 1 6 0 0 0 21 34 1 0 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 23 35 1 0 0 0 0 24 28 1 6 0 0 0 24 33 1 0 0 0 0 25 29 1 6 0 0 0 25 36 1 0 0 0 0 26 31 2 0 0 0 0 26 34 1 0 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 6 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.23
Volume:	507.798
LogP:	5.03
LogD:	3.722
LogS:	-4.458
# Rotatable Bonds:	5
TPSA:	98.5
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	5.381
Fsp3:	0.517
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:	-4.846
MDCK Permeability:	1.6858577509992756e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	95.25659942626953%
Volume Distribution (VD):	1.952
Pgp-substrate:	6.2110595703125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.249
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.31
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	8.805
Half-life (T1/2):	0.462

ADMET: Toxicity

hERG Blockers:	0.823
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.914
Carcinogencity:	0.107
Eye Corrosion:	0.008
Eye Irritation:	0.02
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC238370

Natural Product ID:	NPC238370
*Common Name:**	Malayenolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GAGKMCOQPVBDOW-ZYVBNYDISA-N
Standard InCHI:	InChI=1S/C29H34O7/c1-16-11-12-23(35-27(32)19-9-7-6-8-10-19)28(4)22(14-20-17(2)26(31)34-21(20)13-16)29(5)25(36-29)15-24(28)33-18(3)30/h6-10,13,21-25H,11-12,14-15H2,1-5H3/b16-13-/t21-,22+,23-,24-,25-,28-,29+/m0/s1
SMILES:	C/C/1=C/[C@H]2C(=C(C)C(=O)O2)C[C@@H]2[C@@](C)([C@H](CC1)OC(=O)c1ccccc1)[C@H](C[C@H]1[C@]2(C)O1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452489
PubChem CID:	10601273
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	<	2.0	ug.mL-1	PMID[558924]

☑ 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 NPC238370 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	319
0.1-0.2	1232
0.2-0.3	2325
0.3-0.4	5528
0.4-0.5	11156
0.5-0.6	12410
0.6-0.7	8564
0.7-0.8	958
0.8-0.85	174
0.85-0.9	30
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9219	High Similarity	NPC147561
0.9084	High Similarity	NPC474608
0.9015	High Similarity	NPC66761
0.9015	High Similarity	NPC17877
0.9015	High Similarity	NPC291638
0.9015	High Similarity	NPC472577
0.9015	High Similarity	NPC195647
0.896	High Similarity	NPC50872
0.8881	High Similarity	NPC183122
0.8881	High Similarity	NPC283375
0.8815	High Similarity	NPC210591
0.8815	High Similarity	NPC214550
0.8815	High Similarity	NPC475652
0.8806	High Similarity	NPC472545
0.8806	High Similarity	NPC472551
0.875	High Similarity	NPC171207
0.875	High Similarity	NPC473109
0.875	High Similarity	NPC200592
0.875	High Similarity	NPC473758
0.875	High Similarity	NPC147880
0.875	High Similarity	NPC473085
0.875	High Similarity	NPC473112
0.875	High Similarity	NPC473613
0.875	High Similarity	NPC472547
0.875	High Similarity	NPC476094
0.875	High Similarity	NPC275592
0.875	High Similarity	NPC100913
0.875	High Similarity	NPC184747
0.875	High Similarity	NPC211137
0.875	High Similarity	NPC43241
0.875	High Similarity	NPC48017
0.875	High Similarity	NPC473081
0.875	High Similarity	NPC97667
0.875	High Similarity	NPC90614
0.875	High Similarity	NPC4341
0.875	High Similarity	NPC473060
0.8741	High Similarity	NPC39549
0.8686	High Similarity	NPC27377
0.8686	High Similarity	NPC472576
0.8686	High Similarity	NPC41481
0.8686	High Similarity	NPC16912
0.8686	High Similarity	NPC97947
0.8686	High Similarity	NPC118080
0.8686	High Similarity	NPC87448
0.8686	High Similarity	NPC291599
0.8615	High Similarity	NPC476599
0.8613	High Similarity	NPC477904
0.8613	High Similarity	NPC183270
0.8593	High Similarity	NPC473399
0.8593	High Similarity	NPC473216
0.8561	High Similarity	NPC177340
0.8561	High Similarity	NPC163087
0.8561	High Similarity	NPC191082
0.8561	High Similarity	NPC475429
0.8561	High Similarity	NPC139067
0.8561	High Similarity	NPC147217
0.8561	High Similarity	NPC270498
0.8561	High Similarity	NPC477894
0.8561	High Similarity	NPC246480
0.8561	High Similarity	NPC473673
0.8551	High Similarity	NPC224491
0.854	High Similarity	NPC9905
0.8538	High Similarity	NPC125053
0.8519	High Similarity	NPC48929
0.85	High Similarity	NPC70716
0.85	High Similarity	NPC25768
0.85	High Similarity	NPC11685
0.85	High Similarity	NPC472569
0.85	High Similarity	NPC125106
0.85	High Similarity	NPC472573
0.85	High Similarity	NPC67777
0.85	High Similarity	NPC470152
0.85	High Similarity	NPC34943
0.85	High Similarity	NPC476974
0.85	High Similarity	NPC57628
0.85	High Similarity	NPC163719
0.85	High Similarity	NPC51314
0.85	High Similarity	NPC95265
0.85	High Similarity	NPC472570
0.85	High Similarity	NPC470231
0.85	High Similarity	NPC95810
0.85	High Similarity	NPC188865
0.85	High Similarity	NPC475122
0.85	High Similarity	NPC475759
0.85	High Similarity	NPC241951
0.8489	Intermediate Similarity	NPC183540
0.8489	Intermediate Similarity	NPC192658
0.8489	Intermediate Similarity	NPC34012
0.8489	Intermediate Similarity	NPC472546
0.8478	Intermediate Similarity	NPC162613
0.8478	Intermediate Similarity	NPC87934
0.8473	Intermediate Similarity	NPC275576
0.8467	Intermediate Similarity	NPC475373
0.8451	Intermediate Similarity	NPC132652
0.844	Intermediate Similarity	NPC469349
0.844	Intermediate Similarity	NPC472572
0.844	Intermediate Similarity	NPC177940
0.844	Intermediate Similarity	NPC472575
0.844	Intermediate Similarity	NPC92867
0.844	Intermediate Similarity	NPC471104
0.844	Intermediate Similarity	NPC476973
0.844	Intermediate Similarity	NPC311825
0.844	Intermediate Similarity	NPC472556
0.844	Intermediate Similarity	NPC200471
0.844	Intermediate Similarity	NPC125882
0.844	Intermediate Similarity	NPC471107
0.844	Intermediate Similarity	NPC174982
0.844	Intermediate Similarity	NPC472571
0.844	Intermediate Similarity	NPC472568
0.844	Intermediate Similarity	NPC470157
0.844	Intermediate Similarity	NPC70403
0.844	Intermediate Similarity	NPC470159
0.844	Intermediate Similarity	NPC158663
0.844	Intermediate Similarity	NPC171525
0.844	Intermediate Similarity	NPC184817
0.844	Intermediate Similarity	NPC473088
0.844	Intermediate Similarity	NPC471100
0.844	Intermediate Similarity	NPC29704
0.844	Intermediate Similarity	NPC96903
0.8438	Intermediate Similarity	NPC473243
0.8429	Intermediate Similarity	NPC131966
0.8429	Intermediate Similarity	NPC91703
0.8429	Intermediate Similarity	NPC191387
0.8417	Intermediate Similarity	NPC266374
0.8409	Intermediate Similarity	NPC169913
0.838	Intermediate Similarity	NPC478263
0.838	Intermediate Similarity	NPC48599
0.838	Intermediate Similarity	NPC209592
0.838	Intermediate Similarity	NPC474935
0.838	Intermediate Similarity	NPC240115
0.838	Intermediate Similarity	NPC20255
0.837	Intermediate Similarity	NPC472394
0.8369	Intermediate Similarity	NPC38696
0.8333	Intermediate Similarity	NPC473082
0.8322	Intermediate Similarity	NPC281717
0.8322	Intermediate Similarity	NPC473760
0.8321	Intermediate Similarity	NPC477893
0.831	Intermediate Similarity	NPC478264
0.8298	Intermediate Similarity	NPC95449
0.8296	Intermediate Similarity	NPC470278
0.8271	Intermediate Similarity	NPC470753
0.8271	Intermediate Similarity	NPC473220
0.8264	Intermediate Similarity	NPC471101
0.8264	Intermediate Similarity	NPC266265
0.8264	Intermediate Similarity	NPC476975
0.8264	Intermediate Similarity	NPC473215
0.8264	Intermediate Similarity	NPC301556
0.8264	Intermediate Similarity	NPC270590
0.8264	Intermediate Similarity	NPC92293
0.8261	Intermediate Similarity	NPC472374
0.8261	Intermediate Similarity	NPC472372
0.8252	Intermediate Similarity	NPC473602
0.824	Intermediate Similarity	NPC128368
0.8219	Intermediate Similarity	NPC22571
0.8219	Intermediate Similarity	NPC138641
0.8219	Intermediate Similarity	NPC145649
0.8219	Intermediate Similarity	NPC283875
0.8219	Intermediate Similarity	NPC233581
0.8219	Intermediate Similarity	NPC469647
0.8219	Intermediate Similarity	NPC469648
0.8207	Intermediate Similarity	NPC254558
0.8207	Intermediate Similarity	NPC470245
0.8207	Intermediate Similarity	NPC473214
0.8207	Intermediate Similarity	NPC31829
0.8203	Intermediate Similarity	NPC84129
0.8195	Intermediate Similarity	NPC470765
0.8194	Intermediate Similarity	NPC217918
0.8188	Intermediate Similarity	NPC477896
0.8182	Intermediate Similarity	NPC127857
0.8175	Intermediate Similarity	NPC472656
0.8162	Intermediate Similarity	NPC472418
0.8162	Intermediate Similarity	NPC72915
0.8151	Intermediate Similarity	NPC471103
0.8151	Intermediate Similarity	NPC51602
0.8151	Intermediate Similarity	NPC470153
0.8125	Intermediate Similarity	NPC312393
0.8125	Intermediate Similarity	NPC475552
0.812	Intermediate Similarity	NPC473083
0.8116	Intermediate Similarity	NPC126516
0.8116	Intermediate Similarity	NPC153617
0.8116	Intermediate Similarity	NPC329913
0.8099	Intermediate Similarity	NPC140021
0.8099	Intermediate Similarity	NPC182869
0.8092	Intermediate Similarity	NPC311175
0.8092	Intermediate Similarity	NPC37641
0.8088	Intermediate Similarity	NPC475508
0.8085	Intermediate Similarity	NPC475400
0.8082	Intermediate Similarity	NPC476173
0.8082	Intermediate Similarity	NPC91730
0.8082	Intermediate Similarity	NPC125033
0.8074	Intermediate Similarity	NPC195224
0.8069	Intermediate Similarity	NPC327031
0.8065	Intermediate Similarity	NPC469636
0.8054	Intermediate Similarity	NPC11410
0.8031	Intermediate Similarity	NPC307651
0.803	Intermediate Similarity	NPC70973
0.8028	Intermediate Similarity	NPC473654
0.8027	Intermediate Similarity	NPC197037
0.8027	Intermediate Similarity	NPC469415
0.8027	Intermediate Similarity	NPC472398

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 NPC238370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	817
0.2-0.3	1445
0.3-0.4	2863
0.4-0.5	2274
0.5-0.6	1182
0.6-0.7	288
0.7-0.8	9
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
0.7808	Intermediate Similarity	NPD7236	Approved
0.7795	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2182	Approved
0.755	Intermediate Similarity	NPD7239	Suspended
0.7482	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD164	Approved
0.728	Intermediate Similarity	NPD1238	Approved
0.7246	Intermediate Similarity	NPD6287	Discontinued
0.7231	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7741	Discontinued
0.7203	Intermediate Similarity	NPD7008	Discontinued
0.7195	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2629	Approved
0.7153	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD7799	Discontinued
0.7107	Intermediate Similarity	NPD7058	Phase 2
0.7107	Intermediate Similarity	NPD7057	Phase 3
0.7086	Intermediate Similarity	NPD4628	Phase 3
0.7078	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8368	Discontinued
0.7045	Intermediate Similarity	NPD2067	Discontinued
0.7041	Intermediate Similarity	NPD8407	Phase 2
0.7037	Intermediate Similarity	NPD5951	Approved
0.7015	Intermediate Similarity	NPD6858	Approved
0.7015	Intermediate Similarity	NPD7094	Approved
0.6986	Remote Similarity	NPD7961	Discontinued
0.6981	Remote Similarity	NPD7819	Suspended
0.698	Remote Similarity	NPD3748	Approved
0.6974	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD8434	Phase 2
0.6933	Remote Similarity	NPD2935	Discontinued
0.6912	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6832	Phase 2
0.6861	Remote Similarity	NPD4198	Discontinued
0.6846	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1930	Approved
0.6846	Remote Similarity	NPD1929	Approved
0.6835	Remote Similarity	NPD9545	Approved
0.6831	Remote Similarity	NPD6637	Approved
0.6824	Remote Similarity	NPD2979	Phase 3
0.6824	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2534	Approved
0.6795	Remote Similarity	NPD2532	Approved
0.6795	Remote Similarity	NPD2533	Approved
0.6792	Remote Similarity	NPD6599	Discontinued
0.6786	Remote Similarity	NPD5585	Approved
0.6782	Remote Similarity	NPD8361	Approved
0.6782	Remote Similarity	NPD8360	Approved
0.6782	Remote Similarity	NPD8435	Approved
0.6776	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5494	Approved
0.6763	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6663	Approved
0.6757	Remote Similarity	NPD8032	Phase 2
0.6755	Remote Similarity	NPD2799	Discontinued
0.6753	Remote Similarity	NPD7003	Approved
0.6753	Remote Similarity	NPD8166	Discontinued
0.6753	Remote Similarity	NPD3750	Approved
0.6746	Remote Similarity	NPD1202	Approved
0.6738	Remote Similarity	NPD17	Approved
0.6738	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1876	Approved
0.6732	Remote Similarity	NPD970	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8127	Discontinued
0.6718	Remote Similarity	NPD6647	Phase 2
0.6713	Remote Similarity	NPD3972	Approved
0.6712	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD2438	Suspended
0.6692	Remote Similarity	NPD6685	Approved
0.6689	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2569	Approved
0.6689	Remote Similarity	NPD2567	Approved
0.6688	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7768	Phase 2
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5760	Phase 2
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD5909	Discontinued
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD7075	Discontinued
0.6644	Remote Similarity	NPD7713	Phase 3
0.6643	Remote Similarity	NPD7610	Discontinued
0.6643	Remote Similarity	NPD1281	Approved
0.6641	Remote Similarity	NPD1989	Approved
0.6625	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7458	Discontinued
0.6624	Remote Similarity	NPD6799	Approved
0.6621	Remote Similarity	NPD2198	Approved
0.6621	Remote Similarity	NPD2199	Approved
0.662	Remote Similarity	NPD5125	Phase 3
0.662	Remote Similarity	NPD5126	Approved
0.6618	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2066	Phase 3
0.6609	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD920	Approved
0.6603	Remote Similarity	NPD6190	Approved
0.66	Remote Similarity	NPD4307	Phase 2
0.6597	Remote Similarity	NPD1608	Approved
0.6577	Remote Similarity	NPD2313	Discontinued
0.6556	Remote Similarity	NPD8485	Approved
0.6552	Remote Similarity	NPD4359	Approved
0.6549	Remote Similarity	NPD5691	Approved
0.6543	Remote Similarity	NPD7411	Suspended
0.6541	Remote Similarity	NPD1237	Approved
0.6536	Remote Similarity	NPD7305	Phase 1
0.6531	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2798	Approved
0.6531	Remote Similarity	NPD6085	Phase 2
0.6524	Remote Similarity	NPD5402	Approved
0.6524	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3226	Approved
0.651	Remote Similarity	NPD6039	Approved
0.6507	Remote Similarity	NPD5667	Approved
0.6507	Remote Similarity	NPD1283	Approved
0.6506	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD37	Approved
0.6503	Remote Similarity	NPD6801	Discontinued
0.6494	Remote Similarity	NPD2531	Phase 2
0.6494	Remote Similarity	NPD5404	Approved
0.6494	Remote Similarity	NPD1551	Phase 2
0.6494	Remote Similarity	NPD6100	Approved
0.6494	Remote Similarity	NPD5405	Approved
0.6494	Remote Similarity	NPD5408	Approved
0.6494	Remote Similarity	NPD6099	Approved
0.6494	Remote Similarity	NPD5406	Approved
0.6493	Remote Similarity	NPD5048	Discontinued
0.6489	Remote Similarity	NPD7798	Approved
0.6485	Remote Similarity	NPD4966	Approved
0.6485	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4965	Approved
0.6485	Remote Similarity	NPD4967	Phase 2
0.6481	Remote Similarity	NPD4380	Phase 2
0.6478	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD8150	Discontinued
0.6474	Remote Similarity	NPD1243	Approved
0.6474	Remote Similarity	NPD6765	Approved
0.6474	Remote Similarity	NPD7685	Pre-registration
0.6474	Remote Similarity	NPD6764	Approved
0.6471	Remote Similarity	NPD7473	Discontinued
0.6467	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5765	Approved
0.6463	Remote Similarity	NPD3267	Approved
0.6463	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2797	Approved
0.6463	Remote Similarity	NPD3266	Approved
0.6456	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD9493	Approved
0.6452	Remote Similarity	NPD9257	Approved
0.6452	Remote Similarity	NPD9259	Approved
0.6448	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7055	Discontinued
0.6442	Remote Similarity	NPD6873	Phase 2
0.6442	Remote Similarity	NPD6385	Approved
0.6442	Remote Similarity	NPD6386	Approved
0.6442	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3024	Approved
0.6434	Remote Similarity	NPD3025	Approved
0.6433	Remote Similarity	NPD4110	Phase 3
0.6433	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7497	Discontinued
0.6429	Remote Similarity	NPD1510	Phase 2
0.6429	Remote Similarity	NPD4766	Approved
0.6429	Remote Similarity	NPD7033	Discontinued
0.6429	Remote Similarity	NPD4308	Phase 3
0.6425	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3817	Phase 2
0.6424	Remote Similarity	NPD4870	Approved
0.6424	Remote Similarity	NPD5353	Approved
0.6423	Remote Similarity	NPD5236	Approved
0.6423	Remote Similarity	NPD5240	Approved
0.6423	Remote Similarity	NPD5239	Approved
0.6423	Remote Similarity	NPD5235	Approved
0.6423	Remote Similarity	NPD5237	Approved
0.6419	Remote Similarity	NPD1019	Discontinued
0.6415	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4806	Approved
0.6414	Remote Similarity	NPD4807	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