NPASS Compound

Structure

NPC310511 OpenBabel07101719252D 40 43 0 0 1 0 0 0 0 0999 V2000 -3.0435 -4.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8466 -5.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1027 -0.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4235 -4.8484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2226 -2.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7339 -3.3687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6802 -3.4913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5735 -2.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0916 -5.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3989 -1.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5526 -1.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9412 -0.1017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3989 -3.9883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0995 -4.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4117 -1.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1705 -3.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0941 -1.0670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3989 -3.0110 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2453 -1.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9759 0.0511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2453 -4.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6646 -2.0165 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0264 -2.7076 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9704 -2.4546 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9648 -1.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4085 -4.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 -2.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5526 -2.5224 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2233 -1.5106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5323 -0.8196 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8616 -3.2134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0916 -1.0565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0916 -3.9883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0160 -2.4866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7844 -0.9784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4645 -4.3426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 -5.4542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2265 -3.6515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6614 -3.1457 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 8 29 1 0 0 0 0 9 37 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 28 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 26 1 0 0 0 0 16 31 2 0 0 0 0 16 38 1 0 0 0 0 17 25 1 0 0 0 0 17 29 1 6 0 0 0 18 27 1 0 0 0 0 18 28 1 6 0 0 0 19 27 1 0 0 0 0 19 32 2 0 0 0 0 20 30 1 6 0 0 0 20 40 1 0 0 0 0 21 33 2 0 0 0 0 21 37 1 0 0 0 0 22 15 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 38 1 1 0 0 0 24 29 1 6 0 0 0 24 39 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 36 2 0 0 0 0 26 39 1 0 0 0 0 28 7 1 6 0 0 0 29 30 1 6 0 0 0 30 15 1 6 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.26
Volume:	562.657
LogP:	2.953
LogD:	1.022
LogS:	-4.525
# Rotatable Bonds:	10
TPSA:	145.8
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.213
Synthetic Accessibility Score:	5.799
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.434
MDCK Permeability:	7.183240086305887e-05
Pgp-inhibitor:	0.356
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.213
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.755

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	59.46558380126953%
Volume Distribution (VD):	0.423
Pgp-substrate:	42.2086296081543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.344
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.284
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	3.893
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.166
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.589
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.432
Maximum Recommended Daily Dose:	0.752
Skin Sensitization:	0.189
Carcinogencity:	0.091
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC310511

Natural Product ID:	NPC310511
*Common Name:**	Turrapubesic Acid B
IUPAC Name:	(1aR,3R,3aR,4R,5R,6R,7aS)-5-acetyloxy-6-[(1S,6R)-6-(2-methoxy-2-oxoethyl)-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-3a-methyl-7-methylidene-4-(2-methylpropanoyloxy)-1a,2,3,4,5,6-hexahydroindeno[3,3a-b]oxirene-3-carboxylic acid
Synonyms:
Standard InCHIKey:	XUQVEMVFVSGBAX-FPPQQUGTSA-N
Standard InCHI:	InChI=1S/C30H40O10/c1-14(2)26(36)39-24-23(38-16(4)31)22(15(3)30-20(40-30)12-17(25(34)35)29(24,30)8)28(7)11-10-19(32)27(5,6)18(28)13-21(33)37-9/h10-11,14,17-18,20,22-24H,3,12-13H2,1-2,4-9H3,(H,34,35)/t17-,18-,20+,22+,23+,24-,28-,29+,30+/m0/s1
SMILES:	COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)[C@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C(C)C)[C@@]2([C@]3(C1=C)O[C@@H]3C[C@H]2C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386311
PubChem CID:	24763696
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids 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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[466163]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[466163]

☑ 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 NPC310511 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	246
0.1-0.2	1436
0.2-0.3	4519
0.3-0.4	7382
0.4-0.5	13272
0.5-0.6	7324
0.6-0.7	6195
0.7-0.8	2104
0.8-0.85	181
0.85-0.9	32
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9298	High Similarity	NPC472667
0.9083	High Similarity	NPC175186
0.9083	High Similarity	NPC104382
0.9052	High Similarity	NPC143755
0.9008	High Similarity	NPC471170
0.8879	High Similarity	NPC470420
0.8833	High Similarity	NPC473635
0.877	High Similarity	NPC231529
0.8739	High Similarity	NPC170538
0.8729	High Similarity	NPC4548
0.8707	High Similarity	NPC470793
0.8678	High Similarity	NPC293112
0.8667	High Similarity	NPC473979
0.8667	High Similarity	NPC11895
0.8644	High Similarity	NPC5292
0.8607	High Similarity	NPC287423
0.8595	High Similarity	NPC81736
0.8595	High Similarity	NPC172154
0.8559	High Similarity	NPC153440
0.8547	High Similarity	NPC190286
0.8547	High Similarity	NPC270478
0.8512	High Similarity	NPC469789
0.8487	Intermediate Similarity	NPC473203
0.8487	Intermediate Similarity	NPC475041
0.8468	Intermediate Similarity	NPC470851
0.8462	Intermediate Similarity	NPC238667
0.8435	Intermediate Similarity	NPC253906
0.843	Intermediate Similarity	NPC23786
0.843	Intermediate Similarity	NPC257017
0.843	Intermediate Similarity	NPC222688
0.843	Intermediate Similarity	NPC269642
0.843	Intermediate Similarity	NPC470265
0.843	Intermediate Similarity	NPC162009
0.8417	Intermediate Similarity	NPC474585
0.8417	Intermediate Similarity	NPC471128
0.8417	Intermediate Similarity	NPC79579
0.8417	Intermediate Similarity	NPC471126
0.8417	Intermediate Similarity	NPC145182
0.8417	Intermediate Similarity	NPC157252
0.8403	Intermediate Similarity	NPC124676
0.8403	Intermediate Similarity	NPC257457
0.8403	Intermediate Similarity	NPC311554
0.8403	Intermediate Similarity	NPC146280
0.839	Intermediate Similarity	NPC154363
0.839	Intermediate Similarity	NPC234858
0.839	Intermediate Similarity	NPC471127
0.8387	Intermediate Similarity	NPC470850
0.8376	Intermediate Similarity	NPC250109
0.8376	Intermediate Similarity	NPC317210
0.8376	Intermediate Similarity	NPC962
0.8361	Intermediate Similarity	NPC473802
0.8361	Intermediate Similarity	NPC472399
0.8361	Intermediate Similarity	NPC204812
0.8348	Intermediate Similarity	NPC469370
0.8348	Intermediate Similarity	NPC471934
0.8347	Intermediate Similarity	NPC46570
0.8347	Intermediate Similarity	NPC52839
0.8347	Intermediate Similarity	NPC67569
0.8333	Intermediate Similarity	NPC475520
0.8333	Intermediate Similarity	NPC305260
0.8333	Intermediate Similarity	NPC471855
0.8333	Intermediate Similarity	NPC270850
0.8333	Intermediate Similarity	NPC476960
0.8333	Intermediate Similarity	NPC236918
0.8333	Intermediate Similarity	NPC156745
0.8319	Intermediate Similarity	NPC469684
0.8319	Intermediate Similarity	NPC10721
0.8319	Intermediate Similarity	NPC474518
0.8293	Intermediate Similarity	NPC241456
0.8293	Intermediate Similarity	NPC8374
0.8293	Intermediate Similarity	NPC32868
0.8293	Intermediate Similarity	NPC473919
0.8293	Intermediate Similarity	NPC8369
0.8293	Intermediate Similarity	NPC145238
0.8293	Intermediate Similarity	NPC473709
0.8293	Intermediate Similarity	NPC469790
0.8279	Intermediate Similarity	NPC107493
0.8276	Intermediate Similarity	NPC472215
0.8276	Intermediate Similarity	NPC472214
0.8264	Intermediate Similarity	NPC329080
0.8264	Intermediate Similarity	NPC475885
0.8264	Intermediate Similarity	NPC472759
0.8264	Intermediate Similarity	NPC109973
0.8264	Intermediate Similarity	NPC474370
0.8264	Intermediate Similarity	NPC476961
0.8264	Intermediate Similarity	NPC251226
0.8264	Intermediate Similarity	NPC472004
0.825	Intermediate Similarity	NPC159928
0.825	Intermediate Similarity	NPC118638
0.825	Intermediate Similarity	NPC171905
0.825	Intermediate Similarity	NPC472397
0.825	Intermediate Similarity	NPC473720
0.825	Intermediate Similarity	NPC471125
0.825	Intermediate Similarity	NPC472758
0.8246	Intermediate Similarity	NPC470979
0.8246	Intermediate Similarity	NPC103088
0.8246	Intermediate Similarity	NPC470975
0.824	Intermediate Similarity	NPC473620
0.8235	Intermediate Similarity	NPC298278
0.8235	Intermediate Similarity	NPC477509
0.8235	Intermediate Similarity	NPC148458
0.8235	Intermediate Similarity	NPC176840
0.8235	Intermediate Similarity	NPC270958
0.8235	Intermediate Similarity	NPC49492
0.8235	Intermediate Similarity	NPC266728
0.8226	Intermediate Similarity	NPC471939
0.8226	Intermediate Similarity	NPC470973
0.822	Intermediate Similarity	NPC471204
0.822	Intermediate Similarity	NPC472757
0.8205	Intermediate Similarity	NPC469655
0.8205	Intermediate Similarity	NPC474846
0.8205	Intermediate Similarity	NPC474229
0.8205	Intermediate Similarity	NPC469656
0.8197	Intermediate Similarity	NPC471999
0.8197	Intermediate Similarity	NPC472401
0.8197	Intermediate Similarity	NPC4021
0.8197	Intermediate Similarity	NPC159456
0.8197	Intermediate Similarity	NPC472000
0.8189	Intermediate Similarity	NPC472769
0.8182	Intermediate Similarity	NPC61520
0.8182	Intermediate Similarity	NPC264954
0.8182	Intermediate Similarity	NPC471108
0.8182	Intermediate Similarity	NPC5989
0.8182	Intermediate Similarity	NPC470186
0.8182	Intermediate Similarity	NPC255081
0.8182	Intermediate Similarity	NPC22628
0.8182	Intermediate Similarity	NPC275696
0.8182	Intermediate Similarity	NPC312536
0.8182	Intermediate Similarity	NPC5991
0.8175	Intermediate Similarity	NPC472770
0.8175	Intermediate Similarity	NPC471407
0.8175	Intermediate Similarity	NPC470880
0.8167	Intermediate Similarity	NPC471854
0.8167	Intermediate Similarity	NPC239273
0.816	Intermediate Similarity	NPC42399
0.816	Intermediate Similarity	NPC471940
0.816	Intermediate Similarity	NPC470882
0.816	Intermediate Similarity	NPC473253
0.8151	Intermediate Similarity	NPC178289
0.8151	Intermediate Similarity	NPC472400
0.8145	Intermediate Similarity	NPC473255
0.8142	Intermediate Similarity	NPC22388
0.8136	Intermediate Similarity	NPC280782
0.8136	Intermediate Similarity	NPC475391
0.8136	Intermediate Similarity	NPC471933
0.8136	Intermediate Similarity	NPC100267
0.8136	Intermediate Similarity	NPC71348
0.8136	Intermediate Similarity	NPC475524
0.813	Intermediate Similarity	NPC88326
0.813	Intermediate Similarity	NPC19464
0.813	Intermediate Similarity	NPC153700
0.812	Intermediate Similarity	NPC41551
0.812	Intermediate Similarity	NPC197428
0.812	Intermediate Similarity	NPC76084
0.812	Intermediate Similarity	NPC50223
0.8115	Intermediate Similarity	NPC268530
0.8115	Intermediate Similarity	NPC154491
0.811	Intermediate Similarity	NPC473838
0.811	Intermediate Similarity	NPC475389
0.8103	Intermediate Similarity	NPC472439
0.8103	Intermediate Similarity	NPC469916
0.8099	Intermediate Similarity	NPC475372
0.8099	Intermediate Similarity	NPC50774
0.8099	Intermediate Similarity	NPC329736
0.8099	Intermediate Similarity	NPC284707
0.8099	Intermediate Similarity	NPC709
0.8095	Intermediate Similarity	NPC236999
0.8095	Intermediate Similarity	NPC270109
0.8087	Intermediate Similarity	NPC470980
0.8077	Intermediate Similarity	NPC130447
0.8067	Intermediate Similarity	NPC108721
0.8067	Intermediate Similarity	NPC25909
0.8067	Intermediate Similarity	NPC73300
0.8067	Intermediate Similarity	NPC474937
0.8067	Intermediate Similarity	NPC194100
0.8067	Intermediate Similarity	NPC202889
0.8067	Intermediate Similarity	NPC477126
0.8065	Intermediate Similarity	NPC471392
0.8065	Intermediate Similarity	NPC135038
0.8065	Intermediate Similarity	NPC6193
0.8065	Intermediate Similarity	NPC267822
0.8065	Intermediate Similarity	NPC120724
0.8065	Intermediate Similarity	NPC43252
0.8051	Intermediate Similarity	NPC96739
0.8051	Intermediate Similarity	NPC174471
0.8051	Intermediate Similarity	NPC260786
0.8051	Intermediate Similarity	NPC474871
0.8049	Intermediate Similarity	NPC472001
0.8049	Intermediate Similarity	NPC204731
0.8047	Intermediate Similarity	NPC180902
0.8047	Intermediate Similarity	NPC475139
0.8034	Intermediate Similarity	NPC472216
0.8034	Intermediate Similarity	NPC11710
0.8034	Intermediate Similarity	NPC284828
0.8034	Intermediate Similarity	NPC273433
0.8034	Intermediate Similarity	NPC173905
0.8034	Intermediate Similarity	NPC5475
0.8033	Intermediate Similarity	NPC472933
0.8033	Intermediate Similarity	NPC469380
0.8031	Intermediate Similarity	NPC221414

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 NPC310511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1755
0.2-0.3	3762
0.3-0.4	2235
0.4-0.5	691
0.5-0.6	248
0.6-0.7	161
0.7-0.8	82
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
0.8136	Intermediate Similarity	NPD8297	Approved
0.8087	Intermediate Similarity	NPD6008	Approved
0.8051	Intermediate Similarity	NPD6650	Approved
0.8051	Intermediate Similarity	NPD6649	Approved
0.8017	Intermediate Similarity	NPD7115	Discovery
0.7967	Intermediate Similarity	NPD6319	Approved
0.7966	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6881	Approved
0.7949	Intermediate Similarity	NPD6899	Approved
0.7917	Intermediate Similarity	NPD4632	Approved
0.7881	Intermediate Similarity	NPD6372	Approved
0.7881	Intermediate Similarity	NPD6373	Approved
0.7863	Intermediate Similarity	NPD5697	Approved
0.7833	Intermediate Similarity	NPD6882	Approved
0.7815	Intermediate Similarity	NPD7102	Approved
0.7815	Intermediate Similarity	NPD6883	Approved
0.7815	Intermediate Similarity	NPD7290	Approved
0.7778	Intermediate Similarity	NPD6675	Approved
0.7778	Intermediate Similarity	NPD7604	Phase 2
0.7778	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD7128	Approved
0.7778	Intermediate Similarity	NPD5739	Approved
0.775	Intermediate Similarity	NPD6847	Approved
0.775	Intermediate Similarity	NPD6617	Approved
0.775	Intermediate Similarity	NPD6869	Approved
0.775	Intermediate Similarity	NPD8130	Phase 1
0.7731	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD6013	Approved
0.7731	Intermediate Similarity	NPD6012	Approved
0.7731	Intermediate Similarity	NPD6014	Approved
0.7724	Intermediate Similarity	NPD6009	Approved
0.7717	Intermediate Similarity	NPD7492	Approved
0.7712	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6054	Approved
0.7656	Intermediate Similarity	NPD6616	Approved
0.7656	Intermediate Similarity	NPD7507	Approved
0.7647	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD6011	Approved
0.7619	Intermediate Similarity	NPD5983	Phase 2
0.7615	Intermediate Similarity	NPD7319	Approved
0.7597	Intermediate Similarity	NPD7078	Approved
0.7563	Intermediate Similarity	NPD5701	Approved
0.7559	Intermediate Similarity	NPD6370	Approved
0.7538	Intermediate Similarity	NPD7736	Approved
0.7521	Intermediate Similarity	NPD5211	Phase 2
0.7519	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.748	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD6016	Approved
0.746	Intermediate Similarity	NPD7516	Approved
0.7436	Intermediate Similarity	NPD5344	Discontinued
0.7422	Intermediate Similarity	NPD5988	Approved
0.7414	Intermediate Similarity	NPD7638	Approved
0.7414	Intermediate Similarity	NPD5696	Approved
0.7402	Intermediate Similarity	NPD6059	Approved
0.7398	Intermediate Similarity	NPD6053	Discontinued
0.7395	Intermediate Similarity	NPD5141	Approved
0.7381	Intermediate Similarity	NPD7327	Approved
0.7381	Intermediate Similarity	NPD7328	Approved
0.7377	Intermediate Similarity	NPD4634	Approved
0.7373	Intermediate Similarity	NPD5225	Approved
0.7373	Intermediate Similarity	NPD5226	Approved
0.7373	Intermediate Similarity	NPD5224	Approved
0.7373	Intermediate Similarity	NPD4633	Approved
0.7368	Intermediate Similarity	NPD7260	Phase 2
0.735	Intermediate Similarity	NPD7639	Approved
0.735	Intermediate Similarity	NPD6648	Approved
0.735	Intermediate Similarity	NPD7640	Approved
0.7328	Intermediate Similarity	NPD8293	Discontinued
0.7328	Intermediate Similarity	NPD4755	Approved
0.7323	Intermediate Similarity	NPD7100	Approved
0.7323	Intermediate Similarity	NPD7101	Approved
0.7317	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5174	Approved
0.7311	Intermediate Similarity	NPD5175	Approved
0.7288	Intermediate Similarity	NPD5223	Approved
0.7281	Intermediate Similarity	NPD6399	Phase 3
0.7244	Intermediate Similarity	NPD6335	Approved
0.7236	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD6274	Approved
0.7213	Intermediate Similarity	NPD4730	Approved
0.7213	Intermediate Similarity	NPD4729	Approved
0.7209	Intermediate Similarity	NPD7503	Approved
0.7203	Intermediate Similarity	NPD4700	Approved
0.7193	Intermediate Similarity	NPD6079	Approved
0.7179	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD6083	Phase 2
0.7165	Intermediate Similarity	NPD6317	Approved
0.7155	Intermediate Similarity	NPD5210	Approved
0.7155	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5695	Phase 3
0.7155	Intermediate Similarity	NPD4629	Approved
0.7131	Intermediate Similarity	NPD6412	Phase 2
0.7109	Intermediate Similarity	NPD6313	Approved
0.7109	Intermediate Similarity	NPD6314	Approved
0.7097	Intermediate Similarity	NPD5247	Approved
0.7097	Intermediate Similarity	NPD5250	Approved
0.7097	Intermediate Similarity	NPD5248	Approved
0.7097	Intermediate Similarity	NPD5251	Approved
0.7097	Intermediate Similarity	NPD5249	Phase 3
0.7077	Intermediate Similarity	NPD8296	Approved
0.7077	Intermediate Similarity	NPD8378	Approved
0.7077	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8379	Approved
0.7077	Intermediate Similarity	NPD8380	Approved
0.7077	Intermediate Similarity	NPD8335	Approved
0.7077	Intermediate Similarity	NPD8033	Approved
0.7073	Intermediate Similarity	NPD6686	Approved
0.7049	Intermediate Similarity	NPD4768	Approved
0.7049	Intermediate Similarity	NPD4767	Approved
0.7043	Intermediate Similarity	NPD5284	Approved
0.7043	Intermediate Similarity	NPD5281	Approved
0.7018	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD8294	Approved
0.6992	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4202	Approved
0.6975	Remote Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD6698	Approved
0.6957	Remote Similarity	NPD46	Approved
0.6949	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5221	Approved
0.6949	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD6908	Approved
0.6947	Remote Similarity	NPD6909	Approved
0.6947	Remote Similarity	NPD6921	Approved
0.6935	Remote Similarity	NPD5128	Approved
0.6934	Remote Similarity	NPD6845	Suspended
0.6905	Remote Similarity	NPD5217	Approved
0.6905	Remote Similarity	NPD5216	Approved
0.6905	Remote Similarity	NPD5215	Approved
0.6903	Remote Similarity	NPD6684	Approved
0.6903	Remote Similarity	NPD7146	Approved
0.6903	Remote Similarity	NPD7334	Approved
0.6903	Remote Similarity	NPD6409	Approved
0.6903	Remote Similarity	NPD7521	Approved
0.6903	Remote Similarity	NPD5330	Approved
0.6897	Remote Similarity	NPD5693	Phase 1
0.6891	Remote Similarity	NPD7902	Approved
0.6891	Remote Similarity	NPD5173	Approved
0.6889	Remote Similarity	NPD6033	Approved
0.6885	Remote Similarity	NPD4754	Approved
0.686	Remote Similarity	NPD1700	Approved
0.6842	Remote Similarity	NPD8328	Phase 3
0.6825	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5169	Approved
0.6825	Remote Similarity	NPD5135	Approved
0.6822	Remote Similarity	NPD6868	Approved
0.6814	Remote Similarity	NPD1694	Approved
0.681	Remote Similarity	NPD5785	Approved
0.6807	Remote Similarity	NPD4697	Phase 3
0.6803	Remote Similarity	NPD7632	Discontinued
0.6797	Remote Similarity	NPD8133	Approved
0.6783	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6903	Approved
0.678	Remote Similarity	NPD6001	Approved
0.678	Remote Similarity	NPD7748	Approved
0.6772	Remote Similarity	NPD5127	Approved
0.6754	Remote Similarity	NPD3618	Phase 1
0.6746	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6673	Approved
0.6724	Remote Similarity	NPD4753	Phase 2
0.6724	Remote Similarity	NPD6904	Approved
0.6724	Remote Similarity	NPD6080	Approved
0.6724	Remote Similarity	NPD1695	Approved
0.6723	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3573	Approved
0.6692	Remote Similarity	NPD8515	Approved
0.6692	Remote Similarity	NPD8513	Phase 3
0.6692	Remote Similarity	NPD8517	Approved
0.6692	Remote Similarity	NPD8516	Approved
0.6691	Remote Similarity	NPD8338	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7900	Approved
0.6639	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5737	Approved
0.6638	Remote Similarity	NPD6672	Approved
0.6615	Remote Similarity	NPD5167	Approved
0.661	Remote Similarity	NPD8034	Phase 2
0.661	Remote Similarity	NPD8035	Phase 2
0.661	Remote Similarity	NPD5694	Approved
0.661	Remote Similarity	NPD6050	Approved
0.661	Remote Similarity	NPD7515	Phase 2
0.6609	Remote Similarity	NPD5690	Phase 2
0.6609	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6067	Discontinued
0.6587	Remote Similarity	NPD6614	Approved
0.6579	Remote Similarity	NPD4786	Approved
0.6579	Remote Similarity	NPD3666	Approved
0.6579	Remote Similarity	NPD3133	Approved
0.6579	Remote Similarity	NPD3665	Phase 1
0.6555	Remote Similarity	NPD5778	Approved
0.6555	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD4223	Phase 3
0.6549	Remote Similarity	NPD4221	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