NPASS Compound

Structure

NPC256162 OpenBabel07101718312D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.3164 2.5379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3824 1.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3665 0.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2425 -0.7820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4054 0.6680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1645 2.3672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1486 1.0127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0797 -0.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2425 1.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4835 0.8377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4054 -0.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0476 1.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0797 0.6680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9194 -0.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9194 -1.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2010 0.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5682 -0.7820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8296 2.5422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9168 1.1513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7014 -1.8336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2987 -2.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1203 1.2443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4054 -1.2654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7184 0.6468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5174 1.5924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 6 1 0 0 0 0 2 10 2 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 11 2 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 6 0 0 0 18 25 1 0 0 0 0 19 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.08
Volume:	358.104
LogP:	1.501
LogD:	1.386
LogS:	-3.33
# Rotatable Bonds:	4
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	3.739
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.727
MDCK Permeability:	8.537049325241242e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.22
20% Bioavailability (F20%):	0.298
30% Bioavailability (F30%):	0.322

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	81.82006072998047%
Volume Distribution (VD):	0.451
Pgp-substrate:	24.605817794799805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.37
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.295
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.437
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.567

ADMET: Excretion

Clearance (CL):	1.644
Half-life (T1/2):	0.46

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.702
AMES Toxicity:	0.275
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.081
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC256162

Natural Product ID:	NPC256162
*Common Name:**	(+)-Tylopilusin B
IUPAC Name:	methyl (1R,5R)-1,3,5-trihydroxy-2,5-bis(4-hydroxyphenyl)-4-oxocyclopent-2-ene-1-carboxylate
Synonyms:	(+)-Tylopilusin B
Standard InCHIKey:	IRFBODXJISNYDS-OALUTQOASA-N
Standard InCHI:	InChI=1S/C19H16O8/c1-27-17(24)19(26)14(10-2-6-12(20)7-3-10)15(22)16(23)18(19,25)11-4-8-13(21)9-5-11/h2-9,20-22,25-26H,1H3/t18-,19-/m0/s1
SMILES:	COC(=O)[C@@]1(O)C(=C(C(=O)[C@@]1(O)c1ccc(cc1)O)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208232
PubChem CID:	71463266
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO32559	tylopilus eximius	Species	Boletaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[23215444]

☑ 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
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[514760]

☑ 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 NPC256162 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	290
0.1-0.2	1223
0.2-0.3	2984
0.3-0.4	6946
0.4-0.5	11384
0.5-0.6	5379
0.6-0.7	10098
0.7-0.8	4341
0.8-0.85	47
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC59775
0.9706	High Similarity	NPC32
0.9706	High Similarity	NPC122491
0.8417	Intermediate Similarity	NPC108553
0.838	Intermediate Similarity	NPC255428
0.8231	Intermediate Similarity	NPC474692
0.8207	Intermediate Similarity	NPC156709
0.8207	Intermediate Similarity	NPC179505
0.8188	Intermediate Similarity	NPC229264
0.8153	Intermediate Similarity	NPC164937
0.8146	Intermediate Similarity	NPC44378
0.8146	Intermediate Similarity	NPC280753
0.8146	Intermediate Similarity	NPC32197
0.8102	Intermediate Similarity	NPC14141
0.8079	Intermediate Similarity	NPC94781
0.8069	Intermediate Similarity	NPC67349
0.8069	Intermediate Similarity	NPC279676
0.8056	Intermediate Similarity	NPC233350
0.8056	Intermediate Similarity	NPC182217
0.8056	Intermediate Similarity	NPC70680
0.803	Intermediate Similarity	NPC221870
0.8026	Intermediate Similarity	NPC240592
0.8026	Intermediate Similarity	NPC117346
0.8014	Intermediate Similarity	NPC214246
0.7986	Intermediate Similarity	NPC68517
0.7949	Intermediate Similarity	NPC475378
0.7947	Intermediate Similarity	NPC221383
0.7947	Intermediate Similarity	NPC283081
0.7947	Intermediate Similarity	NPC299090
0.7947	Intermediate Similarity	NPC322660
0.7947	Intermediate Similarity	NPC143892
0.7943	Intermediate Similarity	NPC217431
0.7935	Intermediate Similarity	NPC477299
0.7926	Intermediate Similarity	NPC104514
0.7917	Intermediate Similarity	NPC471749
0.7911	Intermediate Similarity	NPC130489
0.7911	Intermediate Similarity	NPC208676
0.7908	Intermediate Similarity	NPC120171
0.7905	Intermediate Similarity	NPC136649
0.7899	Intermediate Similarity	NPC68167
0.7899	Intermediate Similarity	NPC469927
0.7899	Intermediate Similarity	NPC139171
0.7895	Intermediate Similarity	NPC192568
0.7895	Intermediate Similarity	NPC471076
0.7891	Intermediate Similarity	NPC283560
0.7891	Intermediate Similarity	NPC24295
0.7881	Intermediate Similarity	NPC205389
0.7875	Intermediate Similarity	NPC161151
0.7867	Intermediate Similarity	NPC304956
0.7867	Intermediate Similarity	NPC183824
0.7862	Intermediate Similarity	NPC106406
0.7857	Intermediate Similarity	NPC127975
0.7857	Intermediate Similarity	NPC289021
0.7857	Intermediate Similarity	NPC158546
0.7847	Intermediate Similarity	NPC327204
0.7847	Intermediate Similarity	NPC323379
0.7843	Intermediate Similarity	NPC161955
0.7843	Intermediate Similarity	NPC96599
0.7842	Intermediate Similarity	NPC236981
0.7838	Intermediate Similarity	NPC474875
0.7838	Intermediate Similarity	NPC205751
0.7838	Intermediate Similarity	NPC26241
0.7838	Intermediate Similarity	NPC476820
0.7838	Intermediate Similarity	NPC295492
0.7838	Intermediate Similarity	NPC274891
0.7838	Intermediate Similarity	NPC476819
0.7838	Intermediate Similarity	NPC242355
0.7838	Intermediate Similarity	NPC303683
0.7834	Intermediate Similarity	NPC123208
0.7815	Intermediate Similarity	NPC210330
0.7815	Intermediate Similarity	NPC53884
0.7815	Intermediate Similarity	NPC258671
0.7806	Intermediate Similarity	NPC478235
0.7806	Intermediate Similarity	NPC95498
0.7806	Intermediate Similarity	NPC205918
0.7806	Intermediate Similarity	NPC246566
0.78	Intermediate Similarity	NPC186296
0.78	Intermediate Similarity	NPC277315
0.78	Intermediate Similarity	NPC258469
0.78	Intermediate Similarity	NPC285550
0.78	Intermediate Similarity	NPC43158
0.78	Intermediate Similarity	NPC192831
0.78	Intermediate Similarity	NPC472016
0.7793	Intermediate Similarity	NPC202743
0.7793	Intermediate Similarity	NPC477281
0.7793	Intermediate Similarity	NPC215484
0.7793	Intermediate Similarity	NPC155209
0.7793	Intermediate Similarity	NPC168799
0.7793	Intermediate Similarity	NPC19719
0.7793	Intermediate Similarity	NPC164172
0.7793	Intermediate Similarity	NPC477280
0.7792	Intermediate Similarity	NPC35097
0.7786	Intermediate Similarity	NPC231767
0.7785	Intermediate Similarity	NPC137501
0.7785	Intermediate Similarity	NPC159387
0.7785	Intermediate Similarity	NPC154262
0.7785	Intermediate Similarity	NPC329997
0.7785	Intermediate Similarity	NPC7518
0.7778	Intermediate Similarity	NPC25484
0.7778	Intermediate Similarity	NPC232583
0.777	Intermediate Similarity	NPC302857
0.777	Intermediate Similarity	NPC142703
0.777	Intermediate Similarity	NPC152942
0.777	Intermediate Similarity	NPC219428
0.777	Intermediate Similarity	NPC37250
0.777	Intermediate Similarity	NPC278068
0.7763	Intermediate Similarity	NPC143246
0.7763	Intermediate Similarity	NPC474268
0.7763	Intermediate Similarity	NPC473147
0.7763	Intermediate Similarity	NPC119773
0.7763	Intermediate Similarity	NPC475539
0.7756	Intermediate Similarity	NPC229354
0.7755	Intermediate Similarity	NPC475955
0.7755	Intermediate Similarity	NPC474726
0.7748	Intermediate Similarity	NPC202391
0.7748	Intermediate Similarity	NPC296659
0.7742	Intermediate Similarity	NPC477100
0.7742	Intermediate Similarity	NPC474620
0.7742	Intermediate Similarity	NPC477098
0.7736	Intermediate Similarity	NPC329743
0.7733	Intermediate Similarity	NPC253481
0.7733	Intermediate Similarity	NPC477335
0.7733	Intermediate Similarity	NPC224389
0.7733	Intermediate Similarity	NPC148080
0.7733	Intermediate Similarity	NPC469623
0.7733	Intermediate Similarity	NPC206095
0.7733	Intermediate Similarity	NPC35702
0.7733	Intermediate Similarity	NPC253722
0.7733	Intermediate Similarity	NPC471027
0.7733	Intermediate Similarity	NPC45307
0.7733	Intermediate Similarity	NPC31751
0.7733	Intermediate Similarity	NPC297517
0.7733	Intermediate Similarity	NPC13818
0.7727	Intermediate Similarity	NPC478236
0.7727	Intermediate Similarity	NPC478234
0.7724	Intermediate Similarity	NPC25581
0.7724	Intermediate Similarity	NPC18074
0.7724	Intermediate Similarity	NPC61
0.7724	Intermediate Similarity	NPC471095
0.7724	Intermediate Similarity	NPC173034
0.7724	Intermediate Similarity	NPC471066
0.7724	Intermediate Similarity	NPC5419
0.7718	Intermediate Similarity	NPC475413
0.7718	Intermediate Similarity	NPC473497
0.7718	Intermediate Similarity	NPC474303
0.7708	Intermediate Similarity	NPC470122
0.7708	Intermediate Similarity	NPC17968
0.7708	Intermediate Similarity	NPC469705
0.7704	Intermediate Similarity	NPC23402
0.7703	Intermediate Similarity	NPC170718
0.7703	Intermediate Similarity	NPC308976
0.7702	Intermediate Similarity	NPC322982
0.7697	Intermediate Similarity	NPC475528
0.7692	Intermediate Similarity	NPC471229
0.7692	Intermediate Similarity	NPC158673
0.7688	Intermediate Similarity	NPC73422
0.7688	Intermediate Similarity	NPC310399
0.7682	Intermediate Similarity	NPC319628
0.7682	Intermediate Similarity	NPC284948
0.7682	Intermediate Similarity	NPC303090
0.7682	Intermediate Similarity	NPC37331
0.7682	Intermediate Similarity	NPC89317
0.7682	Intermediate Similarity	NPC220664
0.7677	Intermediate Similarity	NPC277032
0.7673	Intermediate Similarity	NPC473395
0.7667	Intermediate Similarity	NPC477279
0.7667	Intermediate Similarity	NPC469911
0.7664	Intermediate Similarity	NPC471033
0.7664	Intermediate Similarity	NPC311091
0.7662	Intermediate Similarity	NPC189631
0.7662	Intermediate Similarity	NPC1580
0.7662	Intermediate Similarity	NPC120728
0.766	Intermediate Similarity	NPC85565
0.7658	Intermediate Similarity	NPC317585
0.7658	Intermediate Similarity	NPC471456
0.7655	Intermediate Similarity	NPC198388
0.7655	Intermediate Similarity	NPC476407
0.7651	Intermediate Similarity	NPC31745
0.7651	Intermediate Similarity	NPC220936
0.7643	Intermediate Similarity	NPC210597
0.7643	Intermediate Similarity	NPC257847
0.764	Intermediate Similarity	NPC90336
0.7639	Intermediate Similarity	NPC469549
0.7635	Intermediate Similarity	NPC475549
0.7632	Intermediate Similarity	NPC251062
0.7632	Intermediate Similarity	NPC184464
0.7632	Intermediate Similarity	NPC194938
0.7632	Intermediate Similarity	NPC470130
0.7628	Intermediate Similarity	NPC267117
0.7628	Intermediate Similarity	NPC56204
0.7628	Intermediate Similarity	NPC315520
0.7625	Intermediate Similarity	NPC209473
0.7619	Intermediate Similarity	NPC474895
0.7616	Intermediate Similarity	NPC477275
0.7616	Intermediate Similarity	NPC477278
0.7616	Intermediate Similarity	NPC477277
0.7616	Intermediate Similarity	NPC82467
0.761	Intermediate Similarity	NPC10945
0.7607	Intermediate Similarity	NPC88243
0.76	Intermediate Similarity	NPC191280

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 NPC256162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	782
0.2-0.3	1456
0.3-0.4	2674
0.4-0.5	2252
0.5-0.6	1154
0.6-0.7	500
0.7-0.8	73
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
0.7682	Intermediate Similarity	NPD6190	Approved
0.7586	Intermediate Similarity	NPD3764	Approved
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.7368	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6799	Approved
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD943	Approved
0.7246	Intermediate Similarity	NPD7473	Discontinued
0.7237	Intermediate Similarity	NPD2935	Discontinued
0.7235	Intermediate Similarity	NPD7685	Pre-registration
0.7222	Intermediate Similarity	NPD3817	Phase 2
0.7205	Intermediate Similarity	NPD6801	Discontinued
0.72	Intermediate Similarity	NPD6355	Discontinued
0.7192	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4380	Phase 2
0.7178	Intermediate Similarity	NPD3882	Suspended
0.7163	Intermediate Similarity	NPD9545	Approved
0.7134	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1240	Approved
0.7133	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1164	Approved
0.7123	Intermediate Similarity	NPD1470	Approved
0.7086	Intermediate Similarity	NPD230	Phase 1
0.7075	Intermediate Similarity	NPD5647	Approved
0.7067	Intermediate Similarity	NPD6233	Phase 2
0.7067	Intermediate Similarity	NPD6663	Approved
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7059	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2801	Approved
0.7039	Intermediate Similarity	NPD1607	Approved
0.703	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7027	Intermediate Similarity	NPD5736	Approved
0.7019	Intermediate Similarity	NPD3226	Approved
0.7013	Intermediate Similarity	NPD5405	Approved
0.7013	Intermediate Similarity	NPD5404	Approved
0.7013	Intermediate Similarity	NPD5406	Approved
0.7013	Intermediate Similarity	NPD5408	Approved
0.7012	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6994	Remote Similarity	NPD1934	Approved
0.6987	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6166	Phase 2
0.6982	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2344	Approved
0.6968	Remote Similarity	NPD7266	Discontinued
0.6966	Remote Similarity	NPD1201	Approved
0.6966	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7819	Suspended
0.6948	Remote Similarity	NPD7033	Discontinued
0.6944	Remote Similarity	NPD3019	Approved
0.6944	Remote Similarity	NPD2932	Approved
0.6943	Remote Similarity	NPD3400	Discontinued
0.6943	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3750	Approved
0.6939	Remote Similarity	NPD1876	Approved
0.6937	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD7095	Approved
0.6933	Remote Similarity	NPD7411	Suspended
0.6932	Remote Similarity	NPD8150	Discontinued
0.6928	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD9269	Phase 2
0.6918	Remote Similarity	NPD7390	Discontinued
0.6901	Remote Similarity	NPD3818	Discontinued
0.6901	Remote Similarity	NPD9493	Approved
0.6899	Remote Similarity	NPD2354	Approved
0.6897	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3094	Phase 2
0.6887	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3268	Approved
0.6879	Remote Similarity	NPD2629	Approved
0.6875	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2534	Approved
0.6875	Remote Similarity	NPD2532	Approved
0.6875	Remote Similarity	NPD2533	Approved
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5401	Approved
0.6859	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6005	Phase 3
0.6859	Remote Similarity	NPD6004	Phase 3
0.6859	Remote Similarity	NPD6002	Phase 3
0.6855	Remote Similarity	NPD3300	Phase 2
0.6842	Remote Similarity	NPD4062	Phase 3
0.6842	Remote Similarity	NPD3020	Approved
0.6838	Remote Similarity	NPD5048	Discontinued
0.6835	Remote Similarity	NPD8166	Discontinued
0.6824	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6653	Approved
0.6815	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD1511	Approved
0.6807	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4060	Phase 1
0.6792	Remote Similarity	NPD2309	Approved
0.6788	Remote Similarity	NPD37	Approved
0.6786	Remote Similarity	NPD6234	Discontinued
0.6784	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6797	Phase 2
0.6781	Remote Similarity	NPD4136	Approved
0.6781	Remote Similarity	NPD4135	Approved
0.6781	Remote Similarity	NPD4106	Approved
0.6779	Remote Similarity	NPD2797	Approved
0.6776	Remote Similarity	NPD2313	Discontinued
0.6766	Remote Similarity	NPD7768	Phase 2
0.6763	Remote Similarity	NPD3022	Approved
0.6763	Remote Similarity	NPD3021	Approved
0.6759	Remote Similarity	NPD9268	Approved
0.6759	Remote Similarity	NPD4105	Approved
0.6759	Remote Similarity	NPD4102	Approved
0.6757	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5763	Approved
0.6752	Remote Similarity	NPD5762	Approved
0.675	Remote Similarity	NPD7236	Approved
0.6747	Remote Similarity	NPD7972	Discontinued
0.6743	Remote Similarity	NPD7251	Discontinued
0.6743	Remote Similarity	NPD6559	Discontinued
0.6742	Remote Similarity	NPD2860	Approved
0.6742	Remote Similarity	NPD2859	Approved
0.6733	Remote Similarity	NPD2798	Approved
0.6725	Remote Similarity	NPD3926	Phase 2
0.6724	Remote Similarity	NPD7074	Phase 3
0.6712	Remote Similarity	NPD5306	Approved
0.6712	Remote Similarity	NPD5305	Approved
0.6712	Remote Similarity	NPD17	Approved
0.6711	Remote Similarity	NPD1283	Approved
0.6709	Remote Similarity	NPD4534	Discontinued
0.6709	Remote Similarity	NPD5958	Discontinued
0.6707	Remote Similarity	NPD7458	Discontinued
0.6706	Remote Similarity	NPD7199	Phase 2
0.6705	Remote Similarity	NPD7799	Discontinued
0.6705	Remote Similarity	NPD3751	Discontinued
0.6705	Remote Similarity	NPD7808	Phase 3
0.6691	Remote Similarity	NPD74	Approved
0.6691	Remote Similarity	NPD9266	Approved
0.6689	Remote Similarity	NPD3972	Approved
0.6689	Remote Similarity	NPD1481	Phase 2
0.6688	Remote Similarity	NPD2796	Approved
0.6688	Remote Similarity	NPD1551	Phase 2
0.6687	Remote Similarity	NPD3887	Approved
0.6686	Remote Similarity	NPD5953	Discontinued
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD2934	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6647	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD8455	Phase 2
0.6646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7239	Suspended
0.6646	Remote Similarity	NPD2353	Approved
0.6646	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2346	Discontinued
0.6645	Remote Similarity	NPD4340	Discontinued
0.6645	Remote Similarity	NPD6832	Phase 2
0.6644	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2067	Discontinued
0.6629	Remote Similarity	NPD7472	Approved
0.6626	Remote Similarity	NPD5049	Phase 3
0.6626	Remote Similarity	NPD6273	Approved
0.6625	Remote Similarity	NPD2575	Approved
0.6624	Remote Similarity	NPD3748	Approved
0.6624	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4807	Approved
0.6622	Remote Similarity	NPD4806	Approved
0.6622	Remote Similarity	NPD1535	Discovery
0.6622	Remote Similarity	NPD3092	Approved
0.6619	Remote Similarity	NPD9267	Approved
0.6619	Remote Similarity	NPD9263	Approved
0.6619	Remote Similarity	NPD9264	Approved
0.6612	Remote Similarity	NPD6534	Approved
0.6612	Remote Similarity	NPD6535	Approved
0.6604	Remote Similarity	NPD2424	Discontinued
0.6601	Remote Similarity	NPD3027	Phase 3
0.6597	Remote Similarity	NPD4198	Discontinued

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