NPASS Compound

Structure

CID88958 OpenBabel06191715422D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7812 0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 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 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 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 5.2812 -0.1910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7812 0.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 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 10 1 0 0 0 0 2 19 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 23 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	319.66
LogP:	3.969
LogD:	3.121
LogS:	-6.12
# Rotatable Bonds:	1
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	3.573
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.905
MDCK Permeability:	1.9068491383222863e-05
Pgp-inhibitor:	0.825
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	98.16594696044922%
Volume Distribution (VD):	2.136
Pgp-substrate:	2.7302417755126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.862
CYP2C19-inhibitor:	0.317
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.416
CYP2D6-inhibitor:	0.364
CYP2D6-substrate:	0.429
CYP3A4-inhibitor:	0.807
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	8.767
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.898
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.752
Skin Sensitization:	0.112
Carcinogencity:	0.953
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.168

Download Data

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

Natural Product: NPC88958

Natural Product ID:	NPC88958
*Common Name:**	Isotanshinone Iib
IUPAC Name:	4-(hydroxymethyl)-4,8-dimethyl-2,3-dihydro-1H-naphtho[2,1-f][1]benzofuran-7,11-dione
Synonyms:	Isotanshinone Iib
Standard InCHIKey:	VIDDDTBBUDIKKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-10-8-23-18-14(10)16(21)12-5-6-13-11(15(12)17(18)22)4-3-7-19(13,2)9-20/h5-6,8,20H,3-4,7,9H2,1-2H3
SMILES:	Cc1coc2c1C(=O)c1ccc3c(CCCC3(C)CO)c1C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509426
PubChem CID:	184102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	40.0	%	PMID[570090]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.0	%	PMID[570090]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	4.0	%	PMID[570090]

☑ 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 NPC88958 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	364
0.1-0.2	1598
0.2-0.3	3409
0.3-0.4	9035
0.4-0.5	10581
0.5-0.6	5865
0.6-0.7	7265
0.7-0.8	4472
0.8-0.85	64
0.85-0.9	26
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC179170
0.9595	High Similarity	NPC145830
0.9392	High Similarity	NPC192069
0.9342	High Similarity	NPC221992
0.9257	High Similarity	NPC281398
0.9177	High Similarity	NPC44602
0.9156	High Similarity	NPC299094
0.9156	High Similarity	NPC10051
0.9139	High Similarity	NPC144010
0.9122	High Similarity	NPC114513
0.9122	High Similarity	NPC245522
0.9051	High Similarity	NPC472784
0.8993	High Similarity	NPC27798
0.8993	High Similarity	NPC93241
0.8933	High Similarity	NPC478166
0.8926	High Similarity	NPC117674
0.8896	High Similarity	NPC282793
0.8844	High Similarity	NPC265181
0.8839	High Similarity	NPC469966
0.8831	High Similarity	NPC471613
0.8808	High Similarity	NPC233763
0.8797	High Similarity	NPC472781
0.8797	High Similarity	NPC472782
0.8776	High Similarity	NPC177262
0.8742	High Similarity	NPC472780
0.8742	High Similarity	NPC472783
0.8704	High Similarity	NPC473945
0.8693	High Similarity	NPC252208
0.8671	High Similarity	NPC140952
0.8658	High Similarity	NPC18904
0.8636	High Similarity	NPC280025
0.8608	High Similarity	NPC81405
0.8599	High Similarity	NPC472786
0.8581	High Similarity	NPC226578
0.8553	High Similarity	NPC294300
0.8553	High Similarity	NPC473282
0.8553	High Similarity	NPC317900
0.8553	High Similarity	NPC104380
0.8553	High Similarity	NPC217602
0.8553	High Similarity	NPC476404
0.8481	Intermediate Similarity	NPC75310
0.8431	Intermediate Similarity	NPC53016
0.8421	Intermediate Similarity	NPC263337
0.8418	Intermediate Similarity	NPC44606
0.8408	Intermediate Similarity	NPC472787
0.8385	Intermediate Similarity	NPC287559
0.8385	Intermediate Similarity	NPC472299
0.8365	Intermediate Similarity	NPC23559
0.8365	Intermediate Similarity	NPC290927
0.8354	Intermediate Similarity	NPC475777
0.8344	Intermediate Similarity	NPC56358
0.8344	Intermediate Similarity	NPC202260
0.8344	Intermediate Similarity	NPC472298
0.8333	Intermediate Similarity	NPC18986
0.8333	Intermediate Similarity	NPC478018
0.8323	Intermediate Similarity	NPC472823
0.8313	Intermediate Similarity	NPC478161
0.8313	Intermediate Similarity	NPC478159
0.8301	Intermediate Similarity	NPC52412
0.8293	Intermediate Similarity	NPC121995
0.8293	Intermediate Similarity	NPC475779
0.8269	Intermediate Similarity	NPC224418
0.8261	Intermediate Similarity	NPC304692
0.8258	Intermediate Similarity	NPC185456
0.825	Intermediate Similarity	NPC472785
0.825	Intermediate Similarity	NPC25351
0.8242	Intermediate Similarity	NPC270312
0.8232	Intermediate Similarity	NPC472664
0.8217	Intermediate Similarity	NPC478163
0.821	Intermediate Similarity	NPC474611
0.821	Intermediate Similarity	NPC123153
0.8205	Intermediate Similarity	NPC478019
0.8199	Intermediate Similarity	NPC41880
0.8199	Intermediate Similarity	NPC104736
0.8194	Intermediate Similarity	NPC163948
0.8193	Intermediate Similarity	NPC191012
0.8187	Intermediate Similarity	NPC24232
0.8187	Intermediate Similarity	NPC10429
0.8182	Intermediate Similarity	NPC100849
0.8176	Intermediate Similarity	NPC295914
0.8165	Intermediate Similarity	NPC95526
0.8144	Intermediate Similarity	NPC186392
0.8141	Intermediate Similarity	NPC469385
0.8141	Intermediate Similarity	NPC290038
0.8137	Intermediate Similarity	NPC208806
0.8133	Intermediate Similarity	NPC316262
0.8133	Intermediate Similarity	NPC136641
0.8133	Intermediate Similarity	NPC314653
0.8129	Intermediate Similarity	NPC243577
0.8129	Intermediate Similarity	NPC103134
0.8125	Intermediate Similarity	NPC294511
0.8125	Intermediate Similarity	NPC121615
0.8121	Intermediate Similarity	NPC193998
0.8113	Intermediate Similarity	NPC228842
0.8113	Intermediate Similarity	NPC212257
0.811	Intermediate Similarity	NPC313368
0.8105	Intermediate Similarity	NPC233707
0.8092	Intermediate Similarity	NPC307401
0.8092	Intermediate Similarity	NPC42400
0.8089	Intermediate Similarity	NPC262198
0.8086	Intermediate Similarity	NPC3898
0.8077	Intermediate Similarity	NPC158871
0.8075	Intermediate Similarity	NPC40356
0.8075	Intermediate Similarity	NPC154683
0.8063	Intermediate Similarity	NPC272590
0.8061	Intermediate Similarity	NPC24761
0.8061	Intermediate Similarity	NPC283209
0.8059	Intermediate Similarity	NPC167340
0.8052	Intermediate Similarity	NPC477408
0.8052	Intermediate Similarity	NPC90296
0.8052	Intermediate Similarity	NPC473681
0.8052	Intermediate Similarity	NPC218204
0.8052	Intermediate Similarity	NPC61157
0.805	Intermediate Similarity	NPC211625
0.8049	Intermediate Similarity	NPC476349
0.8049	Intermediate Similarity	NPC476350
0.8047	Intermediate Similarity	NPC313717
0.8047	Intermediate Similarity	NPC315306
0.8038	Intermediate Similarity	NPC302987
0.8038	Intermediate Similarity	NPC250331
0.8037	Intermediate Similarity	NPC7059
0.8037	Intermediate Similarity	NPC247677
0.8037	Intermediate Similarity	NPC160015
0.8036	Intermediate Similarity	NPC472660
0.8026	Intermediate Similarity	NPC46896
0.8026	Intermediate Similarity	NPC217914
0.8025	Intermediate Similarity	NPC158261
0.8025	Intermediate Similarity	NPC41719
0.8025	Intermediate Similarity	NPC42458
0.8024	Intermediate Similarity	NPC41689
0.8013	Intermediate Similarity	NPC69755
0.8013	Intermediate Similarity	NPC64568
0.8012	Intermediate Similarity	NPC246164
0.8012	Intermediate Similarity	NPC472665
0.8	Intermediate Similarity	NPC68848
0.8	Intermediate Similarity	NPC79571
0.8	Intermediate Similarity	NPC473982
0.8	Intermediate Similarity	NPC263432
0.7989	Intermediate Similarity	NPC228209
0.7988	Intermediate Similarity	NPC164110
0.7988	Intermediate Similarity	NPC201127
0.7988	Intermediate Similarity	NPC246647
0.7988	Intermediate Similarity	NPC67197
0.7988	Intermediate Similarity	NPC96342
0.7988	Intermediate Similarity	NPC296957
0.7988	Intermediate Similarity	NPC260902
0.7988	Intermediate Similarity	NPC212967
0.7987	Intermediate Similarity	NPC57552
0.7987	Intermediate Similarity	NPC469425
0.7976	Intermediate Similarity	NPC296558
0.7976	Intermediate Similarity	NPC255787
0.7975	Intermediate Similarity	NPC62799
0.7975	Intermediate Similarity	NPC474261
0.7974	Intermediate Similarity	NPC471670
0.7964	Intermediate Similarity	NPC308156
0.7963	Intermediate Similarity	NPC178932
0.7963	Intermediate Similarity	NPC263676
0.7963	Intermediate Similarity	NPC114880
0.7962	Intermediate Similarity	NPC476944
0.7961	Intermediate Similarity	NPC324117
0.7952	Intermediate Similarity	NPC285567
0.7952	Intermediate Similarity	NPC269117
0.795	Intermediate Similarity	NPC255641
0.795	Intermediate Similarity	NPC290954
0.7949	Intermediate Similarity	NPC473152
0.7939	Intermediate Similarity	NPC8389
0.7939	Intermediate Similarity	NPC472877
0.7935	Intermediate Similarity	NPC148374
0.7935	Intermediate Similarity	NPC1268
0.7935	Intermediate Similarity	NPC470407
0.7931	Intermediate Similarity	NPC475996
0.7931	Intermediate Similarity	NPC472533
0.7929	Intermediate Similarity	NPC302392
0.7927	Intermediate Similarity	NPC194499
0.7927	Intermediate Similarity	NPC474360
0.7927	Intermediate Similarity	NPC180924
0.7925	Intermediate Similarity	NPC300540
0.7925	Intermediate Similarity	NPC71821
0.7925	Intermediate Similarity	NPC471346
0.7922	Intermediate Similarity	NPC471996
0.7922	Intermediate Similarity	NPC301341
0.7922	Intermediate Similarity	NPC284184
0.7919	Intermediate Similarity	NPC59502
0.7917	Intermediate Similarity	NPC473753
0.7917	Intermediate Similarity	NPC473766
0.7917	Intermediate Similarity	NPC279768
0.7914	Intermediate Similarity	NPC214632
0.7914	Intermediate Similarity	NPC469336
0.7914	Intermediate Similarity	NPC281258
0.7908	Intermediate Similarity	NPC22644
0.7905	Intermediate Similarity	NPC184391
0.7904	Intermediate Similarity	NPC476858
0.7904	Intermediate Similarity	NPC476856
0.7904	Intermediate Similarity	NPC476857
0.7904	Intermediate Similarity	NPC475106
0.7901	Intermediate Similarity	NPC175617
0.7901	Intermediate Similarity	NPC156244
0.7901	Intermediate Similarity	NPC470569
0.7898	Intermediate Similarity	NPC267632
0.7898	Intermediate Similarity	NPC329493

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 NPC88958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	993
0.2-0.3	1447
0.3-0.4	2694
0.4-0.5	2176
0.5-0.6	1050
0.6-0.7	362
0.7-0.8	88
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
0.8844	High Similarity	NPD1471	Phase 3
0.8	Intermediate Similarity	NPD3226	Approved
0.7987	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD2346	Discontinued
0.7931	Intermediate Similarity	NPD8434	Phase 2
0.7871	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2309	Approved
0.7697	Intermediate Similarity	NPD5760	Phase 2
0.7697	Intermediate Similarity	NPD5761	Phase 2
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.7593	Intermediate Similarity	NPD6273	Approved
0.759	Intermediate Similarity	NPD7819	Suspended
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.7543	Intermediate Similarity	NPD6765	Approved
0.7543	Intermediate Similarity	NPD6764	Approved
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1247	Approved
0.7517	Intermediate Similarity	NPD3972	Approved
0.7514	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7411	Suspended
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3882	Suspended
0.7391	Intermediate Similarity	NPD7003	Approved
0.7374	Intermediate Similarity	NPD6785	Approved
0.7374	Intermediate Similarity	NPD6784	Approved
0.7353	Intermediate Similarity	NPD7075	Discontinued
0.7353	Intermediate Similarity	NPD3749	Approved
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7458	Discontinued
0.7345	Intermediate Similarity	NPD6559	Discontinued
0.7337	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD920	Approved
0.7329	Intermediate Similarity	NPD2800	Approved
0.7326	Intermediate Similarity	NPD6959	Discontinued
0.7321	Intermediate Similarity	NPD6801	Discontinued
0.7321	Intermediate Similarity	NPD6279	Approved
0.7321	Intermediate Similarity	NPD6280	Approved
0.7317	Intermediate Similarity	NPD2534	Approved
0.7317	Intermediate Similarity	NPD2533	Approved
0.7317	Intermediate Similarity	NPD2532	Approved
0.7317	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD919	Approved
0.729	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6808	Phase 2
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6799	Approved
0.725	Intermediate Similarity	NPD2796	Approved
0.7241	Intermediate Similarity	NPD3926	Phase 2
0.7235	Intermediate Similarity	NPD2296	Approved
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.72	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7236	Approved
0.7195	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1876	Approved
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6232	Discontinued
0.7176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5494	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7159	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD1470	Approved
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4380	Phase 2
0.7099	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7239	Suspended
0.7081	Intermediate Similarity	NPD1510	Phase 2
0.7079	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD1607	Approved
0.7037	Intermediate Similarity	NPD1551	Phase 2
0.7035	Intermediate Similarity	NPD3817	Phase 2
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7025	Intermediate Similarity	NPD3268	Approved
0.702	Intermediate Similarity	NPD1651	Approved
0.7012	Intermediate Similarity	NPD1243	Approved
0.7006	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD7768	Phase 2
0.6983	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8032	Phase 2
0.6978	Remote Similarity	NPD8313	Approved
0.6978	Remote Similarity	NPD8312	Approved
0.6968	Remote Similarity	NPD1283	Approved
0.6962	Remote Similarity	NPD7095	Approved
0.6937	Remote Similarity	NPD4060	Phase 1
0.6937	Remote Similarity	NPD1240	Approved
0.6937	Remote Similarity	NPD4140	Approved
0.6936	Remote Similarity	NPD5402	Approved
0.6927	Remote Similarity	NPD3751	Discontinued
0.6927	Remote Similarity	NPD7177	Discontinued
0.6927	Remote Similarity	NPD3818	Discontinued
0.6923	Remote Similarity	NPD5403	Approved
0.6919	Remote Similarity	NPD1934	Approved
0.6919	Remote Similarity	NPD6844	Discontinued
0.6918	Remote Similarity	NPD3764	Approved
0.6911	Remote Similarity	NPD6778	Approved
0.6911	Remote Similarity	NPD6776	Approved
0.6911	Remote Similarity	NPD6782	Approved
0.6911	Remote Similarity	NPD6780	Approved
0.6911	Remote Similarity	NPD6781	Approved
0.6911	Remote Similarity	NPD6779	Approved
0.6911	Remote Similarity	NPD6777	Approved
0.6905	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5401	Approved
0.6891	Remote Similarity	NPD7435	Discontinued
0.6883	Remote Similarity	NPD1201	Approved
0.6879	Remote Similarity	NPD2801	Approved
0.6871	Remote Similarity	NPD4308	Phase 3
0.6867	Remote Similarity	NPD3750	Approved
0.6864	Remote Similarity	NPD5049	Phase 3
0.6864	Remote Similarity	NPD1512	Approved
0.686	Remote Similarity	NPD5889	Approved
0.686	Remote Similarity	NPD5890	Approved
0.6857	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7008	Discontinued
0.6832	Remote Similarity	NPD2979	Phase 3
0.6831	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6100	Approved
0.6829	Remote Similarity	NPD5406	Approved
0.6829	Remote Similarity	NPD5408	Approved
0.6829	Remote Similarity	NPD5405	Approved
0.6829	Remote Similarity	NPD4476	Approved
0.6829	Remote Similarity	NPD6099	Approved
0.6829	Remote Similarity	NPD5404	Approved
0.6829	Remote Similarity	NPD4477	Approved
0.6826	Remote Similarity	NPD2354	Approved
0.6826	Remote Similarity	NPD3887	Approved
0.6816	Remote Similarity	NPD8404	Phase 2
0.6816	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1203	Approved
0.6815	Remote Similarity	NPD3266	Approved
0.6815	Remote Similarity	NPD3267	Approved
0.6804	Remote Similarity	NPD7697	Approved
0.6804	Remote Similarity	NPD7696	Phase 3
0.6804	Remote Similarity	NPD7698	Approved
0.68	Remote Similarity	NPD5951	Approved
0.6798	Remote Similarity	NPD5711	Approved
0.6798	Remote Similarity	NPD3787	Discontinued
0.6798	Remote Similarity	NPD5710	Approved
0.6791	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8150	Discontinued
0.6774	Remote Similarity	NPD1281	Approved
0.677	Remote Similarity	NPD6233	Phase 2
0.6769	Remote Similarity	NPD7870	Phase 2
0.6769	Remote Similarity	NPD7871	Phase 2
0.6768	Remote Similarity	NPD7033	Discontinued
0.6768	Remote Similarity	NPD3748	Approved
0.6748	Remote Similarity	NPD6651	Approved
0.6747	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7390	Discontinued
0.6746	Remote Similarity	NPD1511	Approved
0.6742	Remote Similarity	NPD8127	Discontinued
0.674	Remote Similarity	NPD7799	Discontinued
0.674	Remote Similarity	NPD2163	Approved
0.6737	Remote Similarity	NPD6535	Approved
0.6737	Remote Similarity	NPD6534	Approved
0.6733	Remote Similarity	NPD1241	Discontinued
0.6731	Remote Similarity	NPD9717	Approved
0.6731	Remote Similarity	NPD1608	Approved
0.6728	Remote Similarity	NPD4307	Phase 2
0.6721	Remote Similarity	NPD5953	Discontinued
0.6721	Remote Similarity	NPD6797	Phase 2
0.6711	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2797	Approved
0.6708	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD411	Approved
0.6706	Remote Similarity	NPD4661	Approved
0.6706	Remote Similarity	NPD4662	Approved
0.6705	Remote Similarity	NPD7058	Phase 2
0.6705	Remote Similarity	NPD6585	Discontinued
0.6705	Remote Similarity	NPD7057	Phase 3
0.6704	Remote Similarity	NPD7229	Phase 3
0.6688	Remote Similarity	NPD5327	Phase 3
0.6688	Remote Similarity	NPD5691	Approved
0.6687	Remote Similarity	NPD2353	Approved
0.6687	Remote Similarity	NPD5735	Approved
0.6687	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5763	Approved
0.6687	Remote Similarity	NPD5762	Approved
0.6685	Remote Similarity	NPD7251	Discontinued
0.6684	Remote Similarity	NPD8285	Discontinued
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9092	Discovery
0.6667	Remote Similarity	NPD3057	Approved
0.6667	Remote Similarity	NPD7961	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