NPASS Compound

Structure

CID104382 OpenBabel06191715452D 42 46 0 0 1 0 0 0 0 0999 V2000 1.1044 0.3821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4256 4.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4652 4.3490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2303 2.5261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7409 3.3737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6841 3.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5759 2.4266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0992 5.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4040 1.0581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5564 1.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1223 2.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9441 0.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4040 3.9942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4123 1.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1723 3.9103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4106 4.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9692 1.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0972 1.0686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4040 3.0155 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2516 1.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9774 -0.0512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2516 4.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0890 2.6327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6656 2.0195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0264 2.7116 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9718 2.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8413 1.0686 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2516 2.5261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5564 2.5261 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2251 1.5129 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5331 0.8208 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8643 3.2182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1026 4.7878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0992 1.0581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0992 3.9942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5333 3.5047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9944 0.1019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2516 5.4623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2269 3.6569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6639 3.1503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5333 1.7606 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 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 8 38 1 0 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 29 1 0 0 0 0 11 17 2 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 15 32 2 0 0 0 0 15 39 1 0 0 0 0 16 33 2 0 0 0 0 16 40 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 1 0 0 0 19 28 1 0 0 0 0 19 29 1 1 0 0 0 20 28 1 0 0 0 0 20 34 2 0 0 0 0 21 31 1 1 0 0 0 21 42 1 0 0 0 0 22 35 2 0 0 0 0 22 38 1 0 0 0 0 23 36 2 0 0 0 0 23 41 1 0 0 0 0 24 14 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 39 1 6 0 0 0 26 30 1 1 0 0 0 26 40 1 0 0 0 0 27 37 1 0 0 0 0 27 41 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 14 1 1 0 0 0 31 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.24
Volume:	577.551
LogP:	2.653
LogD:	1.644
LogS:	-4.376
# Rotatable Bonds:	9
TPSA:	162.1
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	6.051
Fsp3:	0.613
Lipinski Rule-of-5:	Rejected
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:	-5.58
MDCK Permeability:	4.8793623136589304e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	73.94254302978516%
Volume Distribution (VD):	0.504
Pgp-substrate:	26.3496036529541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.463
CYP3A4-substrate:	0.574

ADMET: Excretion

Clearance (CL):	3.589
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.318
Human Hepatotoxicity (H-HT):	0.871
Drug-inuced Liver Injury (DILI):	0.577
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.09
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC104382

Natural Product ID:	NPC104382
*Common Name:**	21-Hydroxytoonacilide
IUPAC Name:	methyl 2-[(1R,2S)-2-[(1aR,3R,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-3-(2-hydroxy-5-oxo-2H-furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:	21-Hydroxytoonacilide
Standard InCHIKey:	XOWAOIDYRGQZSZ-KBLYHONDSA-N
Standard InCHI:	InChI=1S/C31H38O11/c1-14-24(29(6)10-9-20(34)28(4,5)19(29)13-22(35)38-8)25(39-15(2)32)26(40-16(3)33)30(7)18(12-21-31(14,30)42-21)17-11-23(36)41-27(17)37/h9-11,18-19,21,24-27,37H,1,12-13H2,2-8H3/t18-,19-,21+,24+,25+,26-,27?,29-,30+,31+/m0/s1
SMILES:	C=C1[C@H]([C@H]([C@@H]([C@@]2(C)[C@@H](C[C@@H]3[C@]12O3)C1=CC(=O)OC1O)OC(=O)C)OC(=O)C)[C@@]1(C)C=CC(=O)C(C)(C)[C@@H]1CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035090
PubChem CID:	5318362
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
NPO20688	Turraea parvifolia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20688	Turraea parvifolia	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38900.0	nM	PMID[533207]

☑ 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 NPC104382 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	267
0.1-0.2	1516
0.2-0.3	4388
0.3-0.4	7333
0.4-0.5	13453
0.5-0.6	7625
0.6-0.7	6001
0.7-0.8	1993
0.8-0.85	107
0.85-0.9	10
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC175186
0.975	High Similarity	NPC471170
0.9106	High Similarity	NPC470850
0.9083	High Similarity	NPC310511
0.9032	High Similarity	NPC470851
0.874	High Similarity	NPC472769
0.873	High Similarity	NPC472770
0.8629	High Similarity	NPC473979
0.8618	High Similarity	NPC470418
0.8607	High Similarity	NPC472667
0.8605	High Similarity	NPC471234
0.8583	High Similarity	NPC231529
0.8571	High Similarity	NPC287423
0.8571	High Similarity	NPC42399
0.8548	High Similarity	NPC470419
0.8537	High Similarity	NPC143755
0.8525	High Similarity	NPC470420
0.8512	High Similarity	NPC470793
0.8504	High Similarity	NPC473620
0.8504	High Similarity	NPC311534
0.848	Intermediate Similarity	NPC472768
0.8462	Intermediate Similarity	NPC478072
0.845	Intermediate Similarity	NPC471855
0.8438	Intermediate Similarity	NPC473593
0.8438	Intermediate Similarity	NPC471407
0.8387	Intermediate Similarity	NPC4548
0.8372	Intermediate Similarity	NPC476852
0.8361	Intermediate Similarity	NPC471816
0.8359	Intermediate Similarity	NPC476859
0.8359	Intermediate Similarity	NPC270109
0.8346	Intermediate Similarity	NPC293112
0.8333	Intermediate Similarity	NPC27363
0.8333	Intermediate Similarity	NPC469382
0.832	Intermediate Similarity	NPC204731
0.8308	Intermediate Similarity	NPC231240
0.8295	Intermediate Similarity	NPC476851
0.8281	Intermediate Similarity	NPC117702
0.8281	Intermediate Similarity	NPC179412
0.8281	Intermediate Similarity	NPC469757
0.8281	Intermediate Similarity	NPC471357
0.8281	Intermediate Similarity	NPC471356
0.8281	Intermediate Similarity	NPC298841
0.8281	Intermediate Similarity	NPC146456
0.8268	Intermediate Similarity	NPC86346
0.8268	Intermediate Similarity	NPC172154
0.8268	Intermediate Similarity	NPC469379
0.8268	Intermediate Similarity	NPC81736
0.8268	Intermediate Similarity	NPC75856
0.8254	Intermediate Similarity	NPC222688
0.8254	Intermediate Similarity	NPC470265
0.8254	Intermediate Similarity	NPC23786
0.8244	Intermediate Similarity	NPC316915
0.824	Intermediate Similarity	NPC471126
0.824	Intermediate Similarity	NPC241192
0.824	Intermediate Similarity	NPC145182
0.824	Intermediate Similarity	NPC48692
0.824	Intermediate Similarity	NPC471128
0.824	Intermediate Similarity	NPC472004
0.824	Intermediate Similarity	NPC157252
0.8231	Intermediate Similarity	NPC476855
0.8231	Intermediate Similarity	NPC476863
0.8231	Intermediate Similarity	NPC476862
0.8226	Intermediate Similarity	NPC475913
0.8226	Intermediate Similarity	NPC234522
0.8211	Intermediate Similarity	NPC154363
0.8211	Intermediate Similarity	NPC106228
0.8211	Intermediate Similarity	NPC234858
0.8211	Intermediate Similarity	NPC471127
0.8211	Intermediate Similarity	NPC138372
0.8203	Intermediate Similarity	NPC473635
0.8203	Intermediate Similarity	NPC469750
0.8203	Intermediate Similarity	NPC250556
0.8203	Intermediate Similarity	NPC222307
0.8194	Intermediate Similarity	NPC471176
0.8189	Intermediate Similarity	NPC11895
0.8189	Intermediate Similarity	NPC469789
0.8175	Intermediate Similarity	NPC473256
0.8175	Intermediate Similarity	NPC470878
0.8175	Intermediate Similarity	NPC52839
0.8175	Intermediate Similarity	NPC202051
0.8175	Intermediate Similarity	NPC67569
0.8175	Intermediate Similarity	NPC46570
0.8168	Intermediate Similarity	NPC93416
0.8162	Intermediate Similarity	NPC48414
0.8162	Intermediate Similarity	NPC5153
0.816	Intermediate Similarity	NPC19028
0.816	Intermediate Similarity	NPC475041
0.816	Intermediate Similarity	NPC236918
0.816	Intermediate Similarity	NPC156745
0.816	Intermediate Similarity	NPC161065
0.816	Intermediate Similarity	NPC5292
0.816	Intermediate Similarity	NPC9674
0.816	Intermediate Similarity	NPC474179
0.816	Intermediate Similarity	NPC475834
0.8154	Intermediate Similarity	NPC10823
0.8154	Intermediate Similarity	NPC6108
0.8154	Intermediate Similarity	NPC251866
0.8154	Intermediate Similarity	NPC471352
0.8154	Intermediate Similarity	NPC219085
0.8154	Intermediate Similarity	NPC476966
0.8154	Intermediate Similarity	NPC17896
0.8154	Intermediate Similarity	NPC469751
0.8154	Intermediate Similarity	NPC284406
0.8154	Intermediate Similarity	NPC469754
0.8154	Intermediate Similarity	NPC197707
0.8154	Intermediate Similarity	NPC471361
0.8154	Intermediate Similarity	NPC469753
0.8154	Intermediate Similarity	NPC471359
0.8154	Intermediate Similarity	NPC86159
0.8154	Intermediate Similarity	NPC180079
0.8154	Intermediate Similarity	NPC70542
0.8154	Intermediate Similarity	NPC89514
0.8154	Intermediate Similarity	NPC476854
0.8154	Intermediate Similarity	NPC9499
0.8154	Intermediate Similarity	NPC471360
0.8154	Intermediate Similarity	NPC471358
0.8154	Intermediate Similarity	NPC469752
0.8154	Intermediate Similarity	NPC469755
0.8145	Intermediate Similarity	NPC203862
0.8145	Intermediate Similarity	NPC10721
0.814	Intermediate Similarity	NPC329784
0.814	Intermediate Similarity	NPC240070
0.813	Intermediate Similarity	NPC178289
0.8125	Intermediate Similarity	NPC8374
0.8125	Intermediate Similarity	NPC8369
0.8125	Intermediate Similarity	NPC145238
0.811	Intermediate Similarity	NPC170538
0.811	Intermediate Similarity	NPC28532
0.811	Intermediate Similarity	NPC257017
0.811	Intermediate Similarity	NPC269642
0.811	Intermediate Similarity	NPC107493
0.811	Intermediate Similarity	NPC162009
0.8106	Intermediate Similarity	NPC298783
0.8106	Intermediate Similarity	NPC104585
0.8106	Intermediate Similarity	NPC157817
0.8106	Intermediate Similarity	NPC225385
0.8099	Intermediate Similarity	NPC472215
0.8099	Intermediate Similarity	NPC472214
0.8095	Intermediate Similarity	NPC474585
0.8095	Intermediate Similarity	NPC472759
0.8095	Intermediate Similarity	NPC475885
0.8095	Intermediate Similarity	NPC470312
0.8095	Intermediate Similarity	NPC79579
0.8095	Intermediate Similarity	NPC329080
0.8095	Intermediate Similarity	NPC474370
0.8095	Intermediate Similarity	NPC109973
0.8092	Intermediate Similarity	NPC16569
0.8092	Intermediate Similarity	NPC475389
0.8092	Intermediate Similarity	NPC473838
0.8092	Intermediate Similarity	NPC159338
0.8092	Intermediate Similarity	NPC253456
0.8092	Intermediate Similarity	NPC173347
0.8083	Intermediate Similarity	NPC181994
0.808	Intermediate Similarity	NPC472397
0.808	Intermediate Similarity	NPC146280
0.808	Intermediate Similarity	NPC83287
0.808	Intermediate Similarity	NPC171905
0.808	Intermediate Similarity	NPC124676
0.808	Intermediate Similarity	NPC153440
0.808	Intermediate Similarity	NPC471125
0.808	Intermediate Similarity	NPC472758
0.8077	Intermediate Similarity	NPC477490
0.8077	Intermediate Similarity	NPC114306
0.8077	Intermediate Similarity	NPC245094
0.8074	Intermediate Similarity	NPC290746
0.8074	Intermediate Similarity	NPC79250
0.8065	Intermediate Similarity	NPC190286
0.8065	Intermediate Similarity	NPC266728
0.8065	Intermediate Similarity	NPC302471
0.8065	Intermediate Similarity	NPC49492
0.8049	Intermediate Similarity	NPC250109
0.8049	Intermediate Similarity	NPC471173
0.8049	Intermediate Similarity	NPC962
0.8049	Intermediate Similarity	NPC472757
0.8049	Intermediate Similarity	NPC471627
0.8049	Intermediate Similarity	NPC317210
0.8047	Intermediate Similarity	NPC471392
0.8047	Intermediate Similarity	NPC472399
0.8047	Intermediate Similarity	NPC204812
0.8045	Intermediate Similarity	NPC476823
0.8043	Intermediate Similarity	NPC471172
0.8031	Intermediate Similarity	NPC472000
0.8031	Intermediate Similarity	NPC471999
0.8031	Intermediate Similarity	NPC472001
0.803	Intermediate Similarity	NPC180902
0.803	Intermediate Similarity	NPC42670
0.803	Intermediate Similarity	NPC19124
0.803	Intermediate Similarity	NPC475139
0.8016	Intermediate Similarity	NPC473274
0.8016	Intermediate Similarity	NPC255081
0.8016	Intermediate Similarity	NPC275696
0.8016	Intermediate Similarity	NPC471108
0.8016	Intermediate Similarity	NPC473270
0.8016	Intermediate Similarity	NPC22628
0.8016	Intermediate Similarity	NPC5989
0.8016	Intermediate Similarity	NPC5991
0.8016	Intermediate Similarity	NPC264954
0.8016	Intermediate Similarity	NPC469380
0.8015	Intermediate Similarity	NPC140092
0.8015	Intermediate Similarity	NPC232785

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 NPC104382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	1800
0.2-0.3	3730
0.3-0.4	2247
0.4-0.5	678
0.5-0.6	251
0.6-0.7	150
0.7-0.8	67
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
0.8203	Intermediate Similarity	NPD7507	Approved
0.816	Intermediate Similarity	NPD7516	Approved
0.8154	Intermediate Similarity	NPD7319	Approved
0.808	Intermediate Similarity	NPD7328	Approved
0.808	Intermediate Similarity	NPD7327	Approved
0.7857	Intermediate Similarity	NPD7115	Discovery
0.7829	Intermediate Similarity	NPD6370	Approved
0.7803	Intermediate Similarity	NPD7736	Approved
0.7752	Intermediate Similarity	NPD8379	Approved
0.7752	Intermediate Similarity	NPD8378	Approved
0.7752	Intermediate Similarity	NPD8296	Approved
0.7752	Intermediate Similarity	NPD8033	Approved
0.7752	Intermediate Similarity	NPD8380	Approved
0.7752	Intermediate Similarity	NPD8335	Approved
0.7724	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD7492	Approved
0.768	Intermediate Similarity	NPD8297	Approved
0.768	Intermediate Similarity	NPD6882	Approved
0.7674	Intermediate Similarity	NPD6054	Approved
0.7674	Intermediate Similarity	NPD8294	Approved
0.7674	Intermediate Similarity	NPD8377	Approved
0.7661	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD6616	Approved
0.7642	Intermediate Similarity	NPD6686	Approved
0.7615	Intermediate Similarity	NPD7503	Approved
0.7594	Intermediate Similarity	NPD8293	Discontinued
0.7594	Intermediate Similarity	NPD7078	Approved
0.7578	Intermediate Similarity	NPD6009	Approved
0.7538	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.7481	Intermediate Similarity	NPD6015	Approved
0.7481	Intermediate Similarity	NPD6016	Approved
0.748	Intermediate Similarity	NPD6008	Approved
0.748	Intermediate Similarity	NPD4632	Approved
0.746	Intermediate Similarity	NPD6649	Approved
0.746	Intermediate Similarity	NPD6650	Approved
0.7438	Intermediate Similarity	NPD5344	Discontinued
0.7424	Intermediate Similarity	NPD5988	Approved
0.7419	Intermediate Similarity	NPD6412	Phase 2
0.7419	Intermediate Similarity	NPD5697	Approved
0.7419	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6059	Approved
0.7381	Intermediate Similarity	NPD7290	Approved
0.7381	Intermediate Similarity	NPD6883	Approved
0.7381	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD7604	Phase 2
0.736	Intermediate Similarity	NPD7320	Approved
0.7355	Intermediate Similarity	NPD7640	Approved
0.7355	Intermediate Similarity	NPD7639	Approved
0.7339	Intermediate Similarity	NPD7128	Approved
0.7339	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD6402	Approved
0.7339	Intermediate Similarity	NPD6675	Approved
0.7323	Intermediate Similarity	NPD8130	Phase 1
0.7323	Intermediate Similarity	NPD6617	Approved
0.7323	Intermediate Similarity	NPD6869	Approved
0.7323	Intermediate Similarity	NPD6847	Approved
0.7302	Intermediate Similarity	NPD6012	Approved
0.7302	Intermediate Similarity	NPD6014	Approved
0.7302	Intermediate Similarity	NPD6373	Approved
0.7302	Intermediate Similarity	NPD6372	Approved
0.7302	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7266	Intermediate Similarity	NPD6053	Discontinued
0.7236	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD6011	Approved
0.7218	Intermediate Similarity	NPD5983	Phase 2
0.7213	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD5701	Approved
0.7132	Intermediate Similarity	NPD6336	Discontinued
0.712	Intermediate Similarity	NPD5141	Approved
0.7109	Intermediate Similarity	NPD6371	Approved
0.7077	Intermediate Similarity	NPD8133	Approved
0.7073	Intermediate Similarity	NPD5286	Approved
0.7073	Intermediate Similarity	NPD4696	Approved
0.7073	Intermediate Similarity	NPD5285	Approved
0.6985	Remote Similarity	NPD6067	Discontinued
0.6977	Remote Similarity	NPD4634	Approved
0.6963	Remote Similarity	NPD8515	Approved
0.6963	Remote Similarity	NPD8513	Phase 3
0.6963	Remote Similarity	NPD8516	Approved
0.6963	Remote Similarity	NPD8517	Approved
0.696	Remote Similarity	NPD5226	Approved
0.696	Remote Similarity	NPD5225	Approved
0.696	Remote Similarity	NPD4633	Approved
0.696	Remote Similarity	NPD5224	Approved
0.6953	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8338	Approved
0.694	Remote Similarity	NPD7101	Approved
0.694	Remote Similarity	NPD7100	Approved
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6083	Phase 2
0.6911	Remote Similarity	NPD4755	Approved
0.6911	Remote Similarity	NPD6084	Phase 2
0.6906	Remote Similarity	NPD6033	Approved
0.6905	Remote Similarity	NPD5175	Approved
0.6905	Remote Similarity	NPD5174	Approved
0.6899	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5223	Approved
0.6879	Remote Similarity	NPD7260	Phase 2
0.6866	Remote Similarity	NPD6335	Approved
0.6861	Remote Similarity	NPD8328	Phase 3
0.6855	Remote Similarity	NPD4225	Approved
0.6855	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD6274	Approved
0.6833	Remote Similarity	NPD46	Approved
0.6833	Remote Similarity	NPD6698	Approved
0.6825	Remote Similarity	NPD7632	Discontinued
0.6822	Remote Similarity	NPD4729	Approved
0.6822	Remote Similarity	NPD4730	Approved
0.68	Remote Similarity	NPD4700	Approved
0.6791	Remote Similarity	NPD6317	Approved
0.6777	Remote Similarity	NPD6079	Approved
0.6748	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5695	Phase 3
0.6748	Remote Similarity	NPD4629	Approved
0.6748	Remote Similarity	NPD5210	Approved
0.6744	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6314	Approved
0.6741	Remote Similarity	NPD6313	Approved
0.6721	Remote Similarity	NPD4202	Approved
0.6721	Remote Similarity	NPD6399	Phase 3
0.6718	Remote Similarity	NPD5248	Approved
0.6718	Remote Similarity	NPD5247	Approved
0.6718	Remote Similarity	NPD5251	Approved
0.6718	Remote Similarity	NPD5250	Approved
0.6718	Remote Similarity	NPD5249	Phase 3
0.6715	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6612	Remote Similarity	NPD5328	Approved
0.6597	Remote Similarity	NPD6845	Suspended
0.6594	Remote Similarity	NPD6909	Approved
0.6594	Remote Similarity	NPD6908	Approved
0.6587	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5956	Approved
0.6566	Remote Similarity	NPD7799	Discontinued
0.6565	Remote Similarity	NPD5128	Approved
0.656	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5222	Approved
0.656	Remote Similarity	NPD5221	Approved
0.6557	Remote Similarity	NPD7838	Discovery
0.6549	Remote Similarity	NPD8336	Approved
0.6549	Remote Similarity	NPD8337	Approved
0.6544	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5216	Approved
0.6541	Remote Similarity	NPD5215	Approved
0.6541	Remote Similarity	NPD5217	Approved
0.6529	Remote Similarity	NPD6903	Approved
0.6512	Remote Similarity	NPD4754	Approved
0.6508	Remote Similarity	NPD5173	Approved
0.6504	Remote Similarity	NPD5284	Approved
0.6504	Remote Similarity	NPD5281	Approved
0.6504	Remote Similarity	NPD7637	Suspended
0.6504	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD7334	Approved
0.65	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD6684	Approved
0.65	Remote Similarity	NPD5330	Approved
0.65	Remote Similarity	NPD7146	Approved
0.6479	Remote Similarity	NPD8074	Phase 3
0.6475	Remote Similarity	NPD6921	Approved
0.6475	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7625	Phase 1
0.6471	Remote Similarity	NPD6868	Approved
0.6466	Remote Similarity	NPD5169	Approved
0.6466	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5135	Approved
0.6452	Remote Similarity	NPD5778	Approved
0.6452	Remote Similarity	NPD5779	Approved
0.6418	Remote Similarity	NPD5127	Approved
0.6418	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD6001	Approved
0.64	Remote Similarity	NPD7748	Approved
0.6393	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5362	Discontinued
0.6378	Remote Similarity	NPD7902	Approved
0.6376	Remote Similarity	NPD6334	Approved
0.6376	Remote Similarity	NPD6333	Approved
0.6371	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD3618	Phase 1
0.6357	Remote Similarity	NPD1700	Approved
0.6349	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6904	Approved
0.6341	Remote Similarity	NPD1695	Approved
0.6341	Remote Similarity	NPD6080	Approved
0.6341	Remote Similarity	NPD6673	Approved
0.6336	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3666	Approved
0.6333	Remote Similarity	NPD3665	Phase 1
0.6333	Remote Similarity	NPD4786	Approved
0.6333	Remote Similarity	NPD3133	Approved
0.6311	Remote Similarity	NPD4251	Approved
0.6311	Remote Similarity	NPD4250	Approved
0.6311	Remote Similarity	NPD7524	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