NPASS Compound

Structure

CID145830 OpenBabel06191715502D 23 26 0 0 1 0 0 0 0 0999 V2000 0.8363 2.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0282 -2.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8651 -0.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0274 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5138 -1.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3521 -1.9347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8654 -1.4501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8657 -2.4179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1899 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5135 -0.4832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1902 -1.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6749 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3516 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5130 1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3513 0.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6752 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0279 -1.9342 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.5846 -1.7706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5127 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2172 1.4684 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 18 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 17 1 0 0 0 0 16 21 2 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:	3.227
LogD:	2.761
LogS:	-5.418
# 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:	0.821
Synthetic Accessibility Score:	3.626
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:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.804
MDCK Permeability:	1.9050223272643052e-05
Pgp-inhibitor:	0.328
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.449

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	98.58888244628906%
Volume Distribution (VD):	1.787
Pgp-substrate:	1.684106707572937%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.806
CYP2C19-inhibitor:	0.418
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.538
CYP2C9-substrate:	0.398
CYP2D6-inhibitor:	0.499
CYP2D6-substrate:	0.428
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	8.362
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.543
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.628
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.477
Skin Sensitization:	0.164
Carcinogencity:	0.814
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC145830

Natural Product ID:	NPC145830
*Common Name:**	Tanshinone Iib
IUPAC Name:	6-(hydroxymethyl)-1,6-dimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms:	Tanshinone IIB
Standard InCHIKey:	XDUXBBDRILEIEZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-10-8-23-18-12-5-6-13-11(4-3-7-19(13,2)9-20)15(12)17(22)16(21)14(10)18/h5-6,8,20H,3-4,7,9H2,1-2H3
SMILES:	OCC1(C)CCCc2c1ccc1c2C(=O)C(=O)c2c1occ2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL215254
PubChem CID:	318797
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
IC50	7
Ki	1

Activity Type	# Activity
Cell Line	2
Individual Protein	5
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15550.0	nM	PMID[485824]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[485824]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	24800.0	nM	PMID[485825]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	10700.0	nM	PMID[485825]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	Ki	=	21600.0	nM	PMID[485825]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	52000.0	nM	PMID[485825]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	18000.0	nM	PMID[485825]
NPT1123	Protein Complex	EZH2/SUZ12/EED complex	Homo sapiens	IC50	=	4800.0	nM	PMID[485826]

☑ 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 NPC145830 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	347
0.1-0.2	1569
0.2-0.3	3270
0.3-0.4	8786
0.4-0.5	10915
0.5-0.6	5815
0.6-0.7	7319
0.7-0.8	4574
0.8-0.85	67
0.85-0.9	21
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC179170
0.973	High Similarity	NPC221992
0.9653	High Similarity	NPC281398
0.9595	High Similarity	NPC88958
0.9524	High Similarity	NPC144010
0.9404	High Similarity	NPC10051
0.9404	High Similarity	NPC299094
0.9379	High Similarity	NPC93241
0.9379	High Similarity	NPC27798
0.931	High Similarity	NPC117674
0.9	High Similarity	NPC192069
0.8812	High Similarity	NPC44602
0.88	High Similarity	NPC233763
0.8733	High Similarity	NPC114513
0.8733	High Similarity	NPC245522
0.871	High Similarity	NPC23559
0.871	High Similarity	NPC290927
0.8688	High Similarity	NPC472784
0.8675	High Similarity	NPC478166
0.8662	High Similarity	NPC140952
0.8649	High Similarity	NPC18904
0.8645	High Similarity	NPC44606
0.8608	High Similarity	NPC472299
0.8599	High Similarity	NPC81405
0.858	High Similarity	NPC473945
0.8571	High Similarity	NPC472298
0.8543	High Similarity	NPC163948
0.8543	High Similarity	NPC53016
0.8526	High Similarity	NPC282793
0.8526	High Similarity	NPC24232
0.8471	Intermediate Similarity	NPC469966
0.8462	Intermediate Similarity	NPC471613
0.8456	Intermediate Similarity	NPC265181
0.8442	Intermediate Similarity	NPC478018
0.8442	Intermediate Similarity	NPC252208
0.8438	Intermediate Similarity	NPC472782
0.8438	Intermediate Similarity	NPC472781
0.8428	Intermediate Similarity	NPC123153
0.8411	Intermediate Similarity	NPC263337
0.8408	Intermediate Similarity	NPC10429
0.8389	Intermediate Similarity	NPC177262
0.8387	Intermediate Similarity	NPC95526
0.8385	Intermediate Similarity	NPC24761
0.8385	Intermediate Similarity	NPC472783
0.8385	Intermediate Similarity	NPC472780
0.8383	Intermediate Similarity	NPC295914
0.8375	Intermediate Similarity	NPC287559
0.8366	Intermediate Similarity	NPC290038
0.8355	Intermediate Similarity	NPC69755
0.8354	Intermediate Similarity	NPC158261
0.8354	Intermediate Similarity	NPC42458
0.8344	Intermediate Similarity	NPC136641
0.8333	Intermediate Similarity	NPC233707
0.8333	Intermediate Similarity	NPC202260
0.8333	Intermediate Similarity	NPC226578
0.8333	Intermediate Similarity	NPC56358
0.8323	Intermediate Similarity	NPC18986
0.8313	Intermediate Similarity	NPC473282
0.8313	Intermediate Similarity	NPC317900
0.8313	Intermediate Similarity	NPC294300
0.8313	Intermediate Similarity	NPC217602
0.8313	Intermediate Similarity	NPC104380
0.8313	Intermediate Similarity	NPC476404
0.8312	Intermediate Similarity	NPC478019
0.8301	Intermediate Similarity	NPC158871
0.8289	Intermediate Similarity	NPC52412
0.8282	Intermediate Similarity	NPC121995
0.8282	Intermediate Similarity	NPC100849
0.8269	Intermediate Similarity	NPC280025
0.8261	Intermediate Similarity	NPC476349
0.8261	Intermediate Similarity	NPC476350
0.8258	Intermediate Similarity	NPC224418
0.825	Intermediate Similarity	NPC160015
0.825	Intermediate Similarity	NPC304692
0.825	Intermediate Similarity	NPC247677
0.8247	Intermediate Similarity	NPC185456
0.8242	Intermediate Similarity	NPC472660
0.8239	Intermediate Similarity	NPC25351
0.8239	Intermediate Similarity	NPC472786
0.8239	Intermediate Similarity	NPC208806
0.8232	Intermediate Similarity	NPC270312
0.8232	Intermediate Similarity	NPC41689
0.8221	Intermediate Similarity	NPC472664
0.8219	Intermediate Similarity	NPC57552
0.82	Intermediate Similarity	NPC42400
0.8199	Intermediate Similarity	NPC164110
0.8199	Intermediate Similarity	NPC96342
0.8199	Intermediate Similarity	NPC212967
0.8199	Intermediate Similarity	NPC296957
0.8199	Intermediate Similarity	NPC260902
0.8199	Intermediate Similarity	NPC474611
0.8199	Intermediate Similarity	NPC246647
0.8188	Intermediate Similarity	NPC324117
0.8187	Intermediate Similarity	NPC104736
0.8187	Intermediate Similarity	NPC3898
0.8187	Intermediate Similarity	NPC478161
0.8187	Intermediate Similarity	NPC478159
0.8187	Intermediate Similarity	NPC41880
0.8182	Intermediate Similarity	NPC255787
0.8176	Intermediate Similarity	NPC40356
0.8176	Intermediate Similarity	NPC154683
0.8176	Intermediate Similarity	NPC263676
0.8171	Intermediate Similarity	NPC308156
0.816	Intermediate Similarity	NPC269117
0.8158	Intermediate Similarity	NPC470407
0.8158	Intermediate Similarity	NPC1268
0.8153	Intermediate Similarity	NPC474107
0.8148	Intermediate Similarity	NPC472877
0.8141	Intermediate Similarity	NPC300540
0.8137	Intermediate Similarity	NPC180924
0.8133	Intermediate Similarity	NPC46896
0.8125	Intermediate Similarity	NPC75310
0.8117	Intermediate Similarity	NPC329493
0.8117	Intermediate Similarity	NPC103134
0.8113	Intermediate Similarity	NPC121615
0.8113	Intermediate Similarity	NPC156244
0.8113	Intermediate Similarity	NPC294511
0.8101	Intermediate Similarity	NPC212257
0.8101	Intermediate Similarity	NPC228842
0.8089	Intermediate Similarity	NPC478163
0.8086	Intermediate Similarity	NPC67197
0.8079	Intermediate Similarity	NPC307401
0.8075	Intermediate Similarity	NPC148938
0.8072	Intermediate Similarity	NPC291742
0.8072	Intermediate Similarity	NPC191012
0.8067	Intermediate Similarity	NPC1249
0.8067	Intermediate Similarity	NPC209858
0.8063	Intermediate Similarity	NPC67654
0.8063	Intermediate Similarity	NPC130015
0.8063	Intermediate Similarity	NPC38361
0.8059	Intermediate Similarity	NPC472661
0.8052	Intermediate Similarity	NPC124365
0.8052	Intermediate Similarity	NPC149780
0.805	Intermediate Similarity	NPC290954
0.805	Intermediate Similarity	NPC135303
0.805	Intermediate Similarity	NPC148423
0.805	Intermediate Similarity	NPC472406
0.805	Intermediate Similarity	NPC472787
0.805	Intermediate Similarity	NPC255641
0.8049	Intermediate Similarity	NPC283209
0.8039	Intermediate Similarity	NPC148374
0.8038	Intermediate Similarity	NPC211625
0.8035	Intermediate Similarity	NPC472663
0.8035	Intermediate Similarity	NPC472662
0.8025	Intermediate Similarity	NPC7059
0.8025	Intermediate Similarity	NPC302987
0.8024	Intermediate Similarity	NPC186392
0.8013	Intermediate Similarity	NPC469385
0.8012	Intermediate Similarity	NPC1477
0.8012	Intermediate Similarity	NPC214632
0.8012	Intermediate Similarity	NPC235333
0.8012	Intermediate Similarity	NPC122365
0.8012	Intermediate Similarity	NPC213608
0.8	Intermediate Similarity	NPC470406
0.8	Intermediate Similarity	NPC470569
0.8	Intermediate Similarity	NPC116604
0.8	Intermediate Similarity	NPC267632
0.8	Intermediate Similarity	NPC64568
0.8	Intermediate Similarity	NPC149526
0.8	Intermediate Similarity	NPC475777
0.8	Intermediate Similarity	NPC474417
0.8	Intermediate Similarity	NPC193998
0.7988	Intermediate Similarity	NPC68848
0.7988	Intermediate Similarity	NPC79571
0.7988	Intermediate Similarity	NPC478002
0.7987	Intermediate Similarity	NPC296030
0.7987	Intermediate Similarity	NPC39929
0.7977	Intermediate Similarity	NPC228209
0.7975	Intermediate Similarity	NPC198427
0.7975	Intermediate Similarity	NPC268360
0.7975	Intermediate Similarity	NPC472823
0.7975	Intermediate Similarity	NPC272196
0.7964	Intermediate Similarity	NPC296558
0.7963	Intermediate Similarity	NPC233776
0.7963	Intermediate Similarity	NPC213936
0.7963	Intermediate Similarity	NPC297531
0.7962	Intermediate Similarity	NPC49282
0.7962	Intermediate Similarity	NPC62799
0.7961	Intermediate Similarity	NPC141934
0.7959	Intermediate Similarity	NPC329707
0.7952	Intermediate Similarity	NPC475779
0.795	Intermediate Similarity	NPC164912
0.795	Intermediate Similarity	NPC5871
0.795	Intermediate Similarity	NPC207624
0.795	Intermediate Similarity	NPC114880
0.795	Intermediate Similarity	NPC253872
0.795	Intermediate Similarity	NPC178932
0.7949	Intermediate Similarity	NPC476944
0.7949	Intermediate Similarity	NPC66593
0.7947	Intermediate Similarity	NPC158525
0.7939	Intermediate Similarity	NPC304387
0.7939	Intermediate Similarity	NPC285567
0.7937	Intermediate Similarity	NPC147735
0.7937	Intermediate Similarity	NPC470568
0.7927	Intermediate Similarity	NPC8389
0.7927	Intermediate Similarity	NPC324736
0.7925	Intermediate Similarity	NPC306788
0.7925	Intermediate Similarity	NPC135325
0.7922	Intermediate Similarity	NPC477408
0.7914	Intermediate Similarity	NPC213401

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 NPC145830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	978
0.2-0.3	1380
0.3-0.4	2647
0.4-0.5	2222
0.5-0.6	1128
0.6-0.7	381
0.7-0.8	88
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8456	Intermediate Similarity	NPD1471	Phase 3
0.8217	Intermediate Similarity	NPD3226	Approved
0.8212	Intermediate Similarity	NPD2346	Discontinued
0.8212	Intermediate Similarity	NPD2344	Approved
0.8212	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2309	Approved
0.78	Intermediate Similarity	NPD2313	Discontinued
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7714	Intermediate Similarity	NPD8434	Phase 2
0.7706	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6273	Approved
0.7683	Intermediate Similarity	NPD5761	Phase 2
0.7683	Intermediate Similarity	NPD7819	Suspended
0.7683	Intermediate Similarity	NPD5760	Phase 2
0.7654	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3972	Approved
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD7003	Approved
0.7561	Intermediate Similarity	NPD7411	Suspended
0.7545	Intermediate Similarity	NPD3749	Approved
0.7531	Intermediate Similarity	NPD920	Approved
0.753	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.7515	Intermediate Similarity	NPD6279	Approved
0.7515	Intermediate Similarity	NPD6280	Approved
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6808	Phase 2
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2296	Approved
0.7421	Intermediate Similarity	NPD2800	Approved
0.7417	Intermediate Similarity	NPD2798	Approved
0.7415	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1247	Approved
0.7407	Intermediate Similarity	NPD2533	Approved
0.7407	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2534	Approved
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2532	Approved
0.7407	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6599	Discontinued
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6232	Discontinued
0.7351	Intermediate Similarity	NPD1470	Approved
0.7342	Intermediate Similarity	NPD2796	Approved
0.7341	Intermediate Similarity	NPD7473	Discontinued
0.7285	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5844	Phase 1
0.7251	Intermediate Similarity	NPD5494	Approved
0.725	Intermediate Similarity	NPD1549	Phase 2
0.7233	Intermediate Similarity	NPD1551	Phase 2
0.7233	Intermediate Similarity	NPD2935	Discontinued
0.7232	Intermediate Similarity	NPD6765	Approved
0.7232	Intermediate Similarity	NPD6764	Approved
0.723	Intermediate Similarity	NPD1651	Approved
0.7226	Intermediate Similarity	NPD3268	Approved
0.7225	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD1243	Approved
0.72	Intermediate Similarity	NPD7177	Discontinued
0.7193	Intermediate Similarity	NPD919	Approved
0.7188	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD3882	Suspended
0.7176	Intermediate Similarity	NPD7768	Phase 2
0.7171	Intermediate Similarity	NPD1283	Approved
0.717	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD1607	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7101	Intermediate Similarity	NPD6844	Discontinued
0.7101	Intermediate Similarity	NPD6801	Discontinued
0.7091	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1201	Approved
0.7072	Intermediate Similarity	NPD6784	Approved
0.7072	Intermediate Similarity	NPD6785	Approved
0.707	Intermediate Similarity	NPD8032	Phase 2
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD7008	Discontinued
0.7041	Intermediate Similarity	NPD5889	Approved
0.7041	Intermediate Similarity	NPD5890	Approved
0.703	Intermediate Similarity	NPD6799	Approved
0.7025	Intermediate Similarity	NPD1240	Approved
0.7025	Intermediate Similarity	NPD2979	Phase 3
0.7025	Intermediate Similarity	NPD4140	Approved
0.7019	Intermediate Similarity	NPD5405	Approved
0.7019	Intermediate Similarity	NPD5406	Approved
0.7019	Intermediate Similarity	NPD5404	Approved
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD5408	Approved
0.7013	Intermediate Similarity	NPD1203	Approved
0.7013	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD3267	Approved
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD1934	Approved
0.6981	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1281	Approved
0.6959	Remote Similarity	NPD2801	Approved
0.6957	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7033	Discontinued
0.6951	Remote Similarity	NPD3750	Approved
0.6936	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7390	Discontinued
0.6928	Remote Similarity	NPD9717	Approved
0.6928	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD4307	Phase 2
0.6914	Remote Similarity	NPD4476	Approved
0.6914	Remote Similarity	NPD4477	Approved
0.6909	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD411	Approved
0.6899	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6166	Phase 2
0.6893	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5951	Approved
0.6886	Remote Similarity	NPD4661	Approved
0.6886	Remote Similarity	NPD4662	Approved
0.6882	Remote Similarity	NPD6585	Discontinued
0.6875	Remote Similarity	NPD5710	Approved
0.6875	Remote Similarity	NPD7229	Phase 3
0.6875	Remote Similarity	NPD5711	Approved
0.6867	Remote Similarity	NPD7236	Approved
0.6852	Remote Similarity	NPD3748	Approved
0.6848	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1778	Approved
0.6842	Remote Similarity	NPD8285	Discontinued
0.6832	Remote Similarity	NPD6651	Approved
0.6829	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1511	Approved
0.6824	Remote Similarity	NPD1241	Discontinued
0.6824	Remote Similarity	NPD2651	Approved
0.6824	Remote Similarity	NPD2649	Approved
0.6821	Remote Similarity	NPD5402	Approved
0.6821	Remote Similarity	NPD3817	Phase 2
0.6818	Remote Similarity	NPD8127	Discontinued
0.6816	Remote Similarity	NPD3751	Discontinued
0.681	Remote Similarity	NPD2531	Phase 2
0.681	Remote Similarity	NPD2438	Suspended
0.6806	Remote Similarity	NPD6776	Approved
0.6806	Remote Similarity	NPD6780	Approved
0.6806	Remote Similarity	NPD6782	Approved
0.6806	Remote Similarity	NPD6781	Approved
0.6806	Remote Similarity	NPD6778	Approved
0.6806	Remote Similarity	NPD6777	Approved
0.6806	Remote Similarity	NPD6779	Approved
0.6805	Remote Similarity	NPD5403	Approved
0.6805	Remote Similarity	NPD3873	Phase 3
0.6805	Remote Similarity	NPD3869	Phase 3
0.6803	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.68	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5953	Discontinued
0.6792	Remote Similarity	NPD6798	Discontinued
0.6786	Remote Similarity	NPD5401	Approved
0.678	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5691	Approved
0.6774	Remote Similarity	NPD4287	Approved
0.6774	Remote Similarity	NPD5327	Phase 3
0.677	Remote Similarity	NPD1933	Approved
0.677	Remote Similarity	NPD5735	Approved
0.677	Remote Similarity	NPD447	Suspended
0.677	Remote Similarity	NPD6355	Discontinued
0.6765	Remote Similarity	NPD7239	Suspended
0.6757	Remote Similarity	NPD8150	Discontinued
0.6753	Remote Similarity	NPD1611	Approved
0.6746	Remote Similarity	NPD1512	Approved
0.6732	Remote Similarity	NPD17	Approved
0.6732	Remote Similarity	NPD3019	Approved
0.6732	Remote Similarity	NPD4626	Approved
0.673	Remote Similarity	NPD7095	Approved
0.673	Remote Similarity	NPD4625	Phase 3
0.6726	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2163	Approved
0.672	Remote Similarity	NPD7693	Approved
0.6719	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD9494	Approved
0.6708	Remote Similarity	NPD4060	Phase 1
0.6705	Remote Similarity	NPD7577	Discontinued
0.6702	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7698	Approved
0.6701	Remote Similarity	NPD7435	Discontinued
0.6701	Remote Similarity	NPD7697	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