NPASS Compound

Structure

NPC475130 OpenBabel07101719252D 39 44 0 0 1 0 0 0 0 0999 V2000 -1.5005 -0.7599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9872 1.8913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4288 -0.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2644 -1.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3814 -0.0876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6345 0.4602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 -1.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9104 -1.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 0.8203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8527 -1.2589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 -0.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7864 -1.6567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6006 0.1425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6332 -3.2099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3491 -0.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6345 -0.2599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2757 -1.9669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6685 -2.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1667 1.0434 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6128 -0.2599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8778 -0.5486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1287 0.4337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4422 -1.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8440 -2.0794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1758 0.9092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6128 0.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4146 -1.9789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9972 -0.0747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3438 -2.5063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9579 -3.6497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9330 1.0278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4576 -1.6270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8335 -3.0793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2895 -0.6319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3070 -1.4836 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 1.1758 -0.7088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7047 0.8285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 8 1 0 0 0 0 5 23 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 28 1 0 0 0 0 10 36 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 24 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 30 1 0 0 0 0 15 27 1 0 0 0 0 15 35 1 0 0 0 0 16 29 1 0 0 0 0 16 37 1 0 0 0 0 18 25 1 0 0 0 0 19 31 2 0 0 0 0 20 26 1 6 0 0 0 20 39 1 0 0 0 0 21 27 1 6 0 0 0 21 38 1 0 0 0 0 22 29 1 6 0 0 0 22 38 1 0 0 0 0 23 32 2 0 0 0 0 23 39 1 0 0 0 0 24 33 2 0 0 0 0 24 35 1 0 0 0 0 25 28 1 6 0 0 0 25 34 1 0 0 0 0 26 27 1 1 0 0 0 27 9 1 6 0 0 0 28 19 1 6 0 0 0 28 36 1 0 0 0 0 29 26 1 1 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.23
Volume:	530.885
LogP:	2.091
LogD:	1.564
LogS:	-4.437
# Rotatable Bonds:	2
TPSA:	137.96
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	7.595
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.402
MDCK Permeability:	1.4048801858734805e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.891
Plasma Protein Binding (PPB):	68.89698028564453%
Volume Distribution (VD):	1.056
Pgp-substrate:	18.13890838623047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.556
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.883

ADMET: Excretion

Clearance (CL):	5.704
Half-life (T1/2):	0.838

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.986
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.314
Carcinogencity:	0.622
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.528

Download Data

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

Natural Product: NPC475130

Natural Product ID:	NPC475130
*Common Name:**	14'-Hydroxymitoxin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NXTLPIJHYLFGEX-DOXGSCKNSA-N
Standard InCHI:	InChI=1S/C29H36O10/c1-17-6-9-27-15-35-24(33)12-18-7-10-36-28(25(18)34,19(31)14-30)8-4-3-5-23(32)39-20-13-22(38-21(27)11-17)29(16-37-29)26(20,27)2/h3,5,11-12,20-22,25,30,34H,4,6-10,13-16H2,1-2H3/b5-3+,18-12+/t20-,21-,22-,25-,26-,27-,28-,29+/m1/s1
SMILES:	OCC(=O)[C@@]12CC/C=C/C(=O)O[C@@H]3C[C@@H]4[C@@]5([C@]3([C@@]3(COC(=O)/C=C(/[C@H]2O)CCO1)CCC(=C[C@H]3O4)C)C)OC5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498987
PubChem CID:	44566956
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	Palau	n.a.	PMID[11277768]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027756]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.0000013	nM	PMID[555691]

☑ 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 NPC475130 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	231
0.1-0.2	1319
0.2-0.3	4292
0.3-0.4	8020
0.4-0.5	13450
0.5-0.6	7735
0.6-0.7	6151
0.7-0.8	1331
0.8-0.85	136
0.85-0.9	25
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474286
0.8929	High Similarity	NPC101400
0.8929	High Similarity	NPC101965
0.8839	High Similarity	NPC313921
0.8839	High Similarity	NPC98038
0.8727	High Similarity	NPC472263
0.8727	High Similarity	NPC108682
0.8727	High Similarity	NPC469957
0.8727	High Similarity	NPC469959
0.8684	High Similarity	NPC265290
0.8684	High Similarity	NPC305044
0.8661	High Similarity	NPC50223
0.8661	High Similarity	NPC41551
0.8636	High Similarity	NPC29389
0.8636	High Similarity	NPC93026
0.8636	High Similarity	NPC265502
0.8636	High Similarity	NPC469960
0.8624	High Similarity	NPC232515
0.8624	High Similarity	NPC260809
0.8624	High Similarity	NPC474783
0.8547	High Similarity	NPC477092
0.8532	High Similarity	NPC475986
0.8532	High Similarity	NPC252242
0.8532	High Similarity	NPC475956
0.8519	High Similarity	NPC79631
0.8462	Intermediate Similarity	NPC475401
0.844	Intermediate Similarity	NPC26557
0.8407	Intermediate Similarity	NPC77089
0.8376	Intermediate Similarity	NPC475305
0.8364	Intermediate Similarity	NPC214714
0.8364	Intermediate Similarity	NPC200672
0.8348	Intermediate Similarity	NPC317687
0.8261	Intermediate Similarity	NPC317107
0.8257	Intermediate Similarity	NPC274458
0.8257	Intermediate Similarity	NPC474957
0.8257	Intermediate Similarity	NPC79449
0.8254	Intermediate Similarity	NPC471234
0.8226	Intermediate Similarity	NPC470880
0.8214	Intermediate Similarity	NPC169843
0.8182	Intermediate Similarity	NPC23786
0.8182	Intermediate Similarity	NPC13743
0.8182	Intermediate Similarity	NPC107493
0.8182	Intermediate Similarity	NPC98813
0.8182	Intermediate Similarity	NPC470265
0.8165	Intermediate Similarity	NPC347923
0.8165	Intermediate Similarity	NPC182811
0.8165	Intermediate Similarity	NPC476057
0.8158	Intermediate Similarity	NPC14862
0.8158	Intermediate Similarity	NPC474664
0.8158	Intermediate Similarity	NPC233379
0.8148	Intermediate Similarity	NPC240838
0.8125	Intermediate Similarity	NPC123505
0.812	Intermediate Similarity	NPC287075
0.8103	Intermediate Similarity	NPC475495
0.8099	Intermediate Similarity	NPC67569
0.8099	Intermediate Similarity	NPC46570
0.8091	Intermediate Similarity	NPC65700
0.8087	Intermediate Similarity	NPC15218
0.807	Intermediate Similarity	NPC324327
0.807	Intermediate Similarity	NPC194620
0.807	Intermediate Similarity	NPC326994
0.807	Intermediate Similarity	NPC72813
0.807	Intermediate Similarity	NPC474421
0.8065	Intermediate Similarity	NPC473253
0.8065	Intermediate Similarity	NPC473265
0.8049	Intermediate Similarity	NPC8374
0.8034	Intermediate Similarity	NPC191620
0.8034	Intermediate Similarity	NPC477093
0.8034	Intermediate Similarity	NPC475277
0.8034	Intermediate Similarity	NPC473522
0.8017	Intermediate Similarity	NPC474370
0.8017	Intermediate Similarity	NPC79579
0.8	Intermediate Similarity	NPC55972
0.8	Intermediate Similarity	NPC169888
0.8	Intermediate Similarity	NPC322903
0.8	Intermediate Similarity	NPC327286
0.7982	Intermediate Similarity	NPC475802
0.7982	Intermediate Similarity	NPC16313
0.7982	Intermediate Similarity	NPC9303
0.7967	Intermediate Similarity	NPC469789
0.7965	Intermediate Similarity	NPC472755
0.7951	Intermediate Similarity	NPC472001
0.7934	Intermediate Similarity	NPC5292
0.7934	Intermediate Similarity	NPC264954
0.792	Intermediate Similarity	NPC470882
0.7917	Intermediate Similarity	NPC470492
0.7917	Intermediate Similarity	NPC239273
0.7913	Intermediate Similarity	NPC266514
0.7903	Intermediate Similarity	NPC81736
0.7903	Intermediate Similarity	NPC172154
0.7903	Intermediate Similarity	NPC470922
0.7895	Intermediate Similarity	NPC475676
0.7895	Intermediate Similarity	NPC220964
0.7891	Intermediate Similarity	NPC316915
0.7891	Intermediate Similarity	NPC469673
0.7891	Intermediate Similarity	NPC58029
0.7886	Intermediate Similarity	NPC88326
0.7886	Intermediate Similarity	NPC153700
0.7881	Intermediate Similarity	NPC236217
0.7876	Intermediate Similarity	NPC473596
0.7876	Intermediate Similarity	NPC472754
0.7874	Intermediate Similarity	NPC213634
0.7874	Intermediate Similarity	NPC196921
0.7874	Intermediate Similarity	NPC220757
0.7863	Intermediate Similarity	NPC115257
0.7863	Intermediate Similarity	NPC161816
0.7851	Intermediate Similarity	NPC186525
0.7851	Intermediate Similarity	NPC50774
0.7851	Intermediate Similarity	NPC153440
0.7851	Intermediate Similarity	NPC709
0.784	Intermediate Similarity	NPC293112
0.7833	Intermediate Similarity	NPC148458
0.7829	Intermediate Similarity	NPC476823
0.7826	Intermediate Similarity	NPC472751
0.7826	Intermediate Similarity	NPC472749
0.7823	Intermediate Similarity	NPC120724
0.7815	Intermediate Similarity	NPC159333
0.7812	Intermediate Similarity	NPC34963
0.7812	Intermediate Similarity	NPC231240
0.7807	Intermediate Similarity	NPC4620
0.7805	Intermediate Similarity	NPC470829
0.7805	Intermediate Similarity	NPC472000
0.7805	Intermediate Similarity	NPC471999
0.7805	Intermediate Similarity	NPC473228
0.7797	Intermediate Similarity	NPC470961
0.7797	Intermediate Similarity	NPC71680
0.7795	Intermediate Similarity	NPC35109
0.7795	Intermediate Similarity	NPC471407
0.7788	Intermediate Similarity	NPC472753
0.7787	Intermediate Similarity	NPC61520
0.7787	Intermediate Similarity	NPC473203
0.7778	Intermediate Similarity	NPC475922
0.7778	Intermediate Similarity	NPC287423
0.7769	Intermediate Similarity	NPC167606
0.7769	Intermediate Similarity	NPC286528
0.7769	Intermediate Similarity	NPC140055
0.7769	Intermediate Similarity	NPC20302
0.7768	Intermediate Similarity	NPC475653
0.7768	Intermediate Similarity	NPC212465
0.7768	Intermediate Similarity	NPC177232
0.776	Intermediate Similarity	NPC8369
0.776	Intermediate Similarity	NPC473255
0.7759	Intermediate Similarity	NPC470192
0.775	Intermediate Similarity	NPC216665
0.7742	Intermediate Similarity	NPC269642
0.7739	Intermediate Similarity	NPC472756
0.7739	Intermediate Similarity	NPC472748
0.7734	Intermediate Similarity	NPC241935
0.7734	Intermediate Similarity	NPC279478
0.7731	Intermediate Similarity	NPC241477
0.7724	Intermediate Similarity	NPC474585
0.7719	Intermediate Similarity	NPC49393
0.7719	Intermediate Similarity	NPC105725
0.7719	Intermediate Similarity	NPC39996
0.7712	Intermediate Similarity	NPC29133
0.7712	Intermediate Similarity	NPC89408
0.7712	Intermediate Similarity	NPC5103
0.7712	Intermediate Similarity	NPC257240
0.7712	Intermediate Similarity	NPC15551
0.7705	Intermediate Similarity	NPC329736
0.7705	Intermediate Similarity	NPC13710
0.7705	Intermediate Similarity	NPC288679
0.7698	Intermediate Similarity	NPC473635
0.7692	Intermediate Similarity	NPC264819
0.7692	Intermediate Similarity	NPC472825
0.7686	Intermediate Similarity	NPC190286
0.7686	Intermediate Similarity	NPC470075
0.768	Intermediate Similarity	NPC11895
0.768	Intermediate Similarity	NPC67251
0.7679	Intermediate Similarity	NPC120299
0.7674	Intermediate Similarity	NPC476193
0.7674	Intermediate Similarity	NPC471855
0.7667	Intermediate Similarity	NPC194100
0.7667	Intermediate Similarity	NPC46269
0.7667	Intermediate Similarity	NPC106395
0.7667	Intermediate Similarity	NPC469463
0.7667	Intermediate Similarity	NPC469496
0.7667	Intermediate Similarity	NPC469454
0.7656	Intermediate Similarity	NPC231529
0.7656	Intermediate Similarity	NPC473593
0.7652	Intermediate Similarity	NPC309398
0.7652	Intermediate Similarity	NPC469980
0.7652	Intermediate Similarity	NPC118902
0.7652	Intermediate Similarity	NPC104161
0.7652	Intermediate Similarity	NPC472747
0.7652	Intermediate Similarity	NPC472750
0.7647	Intermediate Similarity	NPC324683
0.7647	Intermediate Similarity	NPC474750
0.7642	Intermediate Similarity	NPC319570
0.7642	Intermediate Similarity	NPC305260
0.7642	Intermediate Similarity	NPC476960
0.7642	Intermediate Similarity	NPC270850
0.7638	Intermediate Similarity	NPC152091
0.7632	Intermediate Similarity	NPC164598
0.7632	Intermediate Similarity	NPC474339
0.7627	Intermediate Similarity	NPC477102
0.7627	Intermediate Similarity	NPC87335
0.7623	Intermediate Similarity	NPC312824
0.7623	Intermediate Similarity	NPC243065
0.7623	Intermediate Similarity	NPC470493

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 NPC475130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1482
0.2-0.3	3721
0.3-0.4	2521
0.4-0.5	724
0.5-0.6	249
0.6-0.7	196
0.7-0.8	60
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7869	Intermediate Similarity	NPD6319	Approved
0.7769	Intermediate Similarity	NPD7115	Discovery
0.7712	Intermediate Similarity	NPD6371	Approved
0.7607	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7492	Approved
0.7455	Intermediate Similarity	NPD6698	Approved
0.7455	Intermediate Similarity	NPD46	Approved
0.744	Intermediate Similarity	NPD6054	Approved
0.7438	Intermediate Similarity	NPD8297	Approved
0.7422	Intermediate Similarity	NPD6616	Approved
0.7364	Intermediate Similarity	NPD7078	Approved
0.7323	Intermediate Similarity	NPD6370	Approved
0.7308	Intermediate Similarity	NPD7736	Approved
0.7297	Intermediate Similarity	NPD5785	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.725	Intermediate Similarity	NPD6881	Approved
0.725	Intermediate Similarity	NPD6686	Approved
0.7244	Intermediate Similarity	NPD6015	Approved
0.7244	Intermediate Similarity	NPD6016	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7217	Intermediate Similarity	NPD6083	Phase 2
0.7217	Intermediate Similarity	NPD6084	Phase 2
0.7213	Intermediate Similarity	NPD6649	Approved
0.7213	Intermediate Similarity	NPD6650	Approved
0.7213	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5988	Approved
0.7167	Intermediate Similarity	NPD5697	Approved
0.7167	Intermediate Similarity	NPD6412	Phase 2
0.7165	Intermediate Similarity	NPD6059	Approved
0.7154	Intermediate Similarity	NPD6053	Discontinued
0.7154	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7132	Intermediate Similarity	NPD7604	Phase 2
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7131	Intermediate Similarity	NPD4634	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7121	Intermediate Similarity	NPD7319	Approved
0.7109	Intermediate Similarity	NPD8033	Approved
0.7109	Intermediate Similarity	NPD7503	Approved
0.7099	Intermediate Similarity	NPD8293	Discontinued
0.7094	Intermediate Similarity	NPD7639	Approved
0.7094	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD5739	Approved
0.7083	Intermediate Similarity	NPD6675	Approved
0.7083	Intermediate Similarity	NPD6402	Approved
0.7083	Intermediate Similarity	NPD7128	Approved
0.7073	Intermediate Similarity	NPD6617	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7073	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD8130	Phase 1
0.7063	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD6013	Approved
0.7049	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD6012	Approved
0.7049	Intermediate Similarity	NPD6373	Approved
0.7043	Intermediate Similarity	NPD5695	Phase 3
0.7023	Intermediate Similarity	NPD7507	Approved
0.7009	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8516	Approved
0.6977	Remote Similarity	NPD8513	Phase 3
0.6977	Remote Similarity	NPD5983	Phase 2
0.6977	Remote Similarity	NPD8517	Approved
0.6977	Remote Similarity	NPD8515	Approved
0.6967	Remote Similarity	NPD7320	Approved
0.6967	Remote Similarity	NPD6011	Approved
0.6911	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8294	Approved
0.6899	Remote Similarity	NPD8377	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD5344	Discontinued
0.6889	Remote Similarity	NPD7260	Phase 2
0.6885	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD7328	Approved
0.6875	Remote Similarity	NPD7327	Approved
0.687	Remote Similarity	NPD8328	Phase 3
0.6864	Remote Similarity	NPD4225	Approved
0.6864	Remote Similarity	NPD5696	Approved
0.6847	Remote Similarity	NPD5363	Approved
0.6846	Remote Similarity	NPD8379	Approved
0.6846	Remote Similarity	NPD8378	Approved
0.6846	Remote Similarity	NPD8380	Approved
0.6846	Remote Similarity	NPD8335	Approved
0.6846	Remote Similarity	NPD8296	Approved
0.6833	Remote Similarity	NPD5211	Phase 2
0.6829	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7516	Approved
0.6815	Remote Similarity	NPD5956	Approved
0.681	Remote Similarity	NPD5282	Discontinued
0.6783	Remote Similarity	NPD7983	Approved
0.6783	Remote Similarity	NPD5693	Phase 1
0.6726	Remote Similarity	NPD4250	Approved
0.6726	Remote Similarity	NPD4251	Approved
0.6721	Remote Similarity	NPD5141	Approved
0.672	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8074	Phase 3
0.6697	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4822	Approved
0.6697	Remote Similarity	NPD4819	Approved
0.6697	Remote Similarity	NPD4821	Approved
0.6697	Remote Similarity	NPD4820	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6692	Remote Similarity	NPD4522	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6638	Remote Similarity	NPD7637	Suspended
0.6637	Remote Similarity	NPD4249	Approved
0.6615	Remote Similarity	NPD6335	Approved
0.661	Remote Similarity	NPD4629	Approved
0.661	Remote Similarity	NPD5210	Approved
0.661	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6904	Approved
0.6609	Remote Similarity	NPD4753	Phase 2
0.6609	Remote Similarity	NPD6080	Approved
0.6609	Remote Similarity	NPD6673	Approved
0.6589	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD5779	Approved
0.6581	Remote Similarity	NPD5778	Approved
0.6577	Remote Similarity	NPD4270	Approved
0.6577	Remote Similarity	NPD4269	Approved
0.6562	Remote Similarity	NPD8133	Approved
0.6557	Remote Similarity	NPD5226	Approved
0.6557	Remote Similarity	NPD4633	Approved
0.6557	Remote Similarity	NPD7632	Discontinued
0.6557	Remote Similarity	NPD5224	Approved
0.6557	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6648	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6522	Remote Similarity	NPD5737	Approved
0.6514	Remote Similarity	NPD4268	Approved
0.6514	Remote Similarity	NPD4271	Approved
0.6504	Remote Similarity	NPD5175	Approved
0.6504	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD4755	Approved
0.6496	Remote Similarity	NPD5694	Approved
0.6496	Remote Similarity	NPD6411	Approved
0.6496	Remote Similarity	NPD6050	Approved
0.6493	Remote Similarity	NPD7830	Approved
0.6493	Remote Similarity	NPD7829	Approved
0.6491	Remote Similarity	NPD7521	Approved
0.6491	Remote Similarity	NPD5786	Approved
0.6491	Remote Similarity	NPD7334	Approved
0.6491	Remote Similarity	NPD5330	Approved
0.6491	Remote Similarity	NPD7146	Approved
0.6491	Remote Similarity	NPD6684	Approved
0.6491	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD6314	Approved
0.6489	Remote Similarity	NPD6313	Approved
0.6486	Remote Similarity	NPD5369	Approved
0.648	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6845	Suspended
0.6475	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6429	Remote Similarity	NPD6435	Approved
0.641	Remote Similarity	NPD5692	Phase 3
0.6408	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4252	Approved
0.6393	Remote Similarity	NPD4700	Approved
0.6379	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD5362	Discontinued
0.6372	Remote Similarity	NPD7154	Phase 3
0.637	Remote Similarity	NPD7642	Approved
0.6356	Remote Similarity	NPD5281	Approved
0.6356	Remote Similarity	NPD5284	Approved
0.6348	Remote Similarity	NPD6098	Approved
0.6348	Remote Similarity	NPD5690	Phase 2
0.6343	Remote Similarity	NPD6909	Approved
0.6343	Remote Similarity	NPD6908	Approved
0.6343	Remote Similarity	NPD6921	Approved
0.6328	Remote Similarity	NPD5250	Approved
0.6328	Remote Similarity	NPD5247	Approved
0.6328	Remote Similarity	NPD5251	Approved
0.6328	Remote Similarity	NPD5248	Approved
0.6328	Remote Similarity	NPD5249	Phase 3
0.6325	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD1695	Approved
0.6325	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD3133	Approved
0.6283	Remote Similarity	NPD5209	Approved
0.6281	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8273	Phase 1
0.627	Remote Similarity	NPD4767	Approved
0.627	Remote Similarity	NPD4768	Approved
0.6261	Remote Similarity	NPD5329	Approved
0.6261	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD5368	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