NPASS Compound

Structure

NPC34056 OpenBabel07101719252D 39 42 0 0 1 0 0 0 0 0999 V2000 -2.3248 1.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1851 -2.5776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0720 -2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4989 -0.7584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0105 -1.6043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9579 -1.7268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3500 -0.9119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3680 -4.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2472 1.5609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7175 1.4082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6763 0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4811 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8304 0.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1718 -0.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6763 -2.2235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7637 -1.4082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6341 0.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7584 -2.8304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3813 -1.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6109 -0.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6907 0.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8703 0.4434 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6763 -1.2468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5222 0.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5222 -2.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8869 -0.5056 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1963 -1.1963 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2528 -0.9435 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5222 -0.7584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8304 -0.7584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0112 -3.7738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6341 -0.4379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3680 0.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3680 -2.2235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5222 -3.6886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7284 -1.5609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4491 -2.1397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4379 -1.6341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 30 1 0 0 0 0 14 37 1 0 0 0 0 15 23 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 37 1 0 0 0 0 17 21 1 0 0 0 0 18 32 2 0 0 0 0 18 38 1 0 0 0 0 19 33 2 0 0 0 0 19 39 1 0 0 0 0 20 22 1 0 0 0 0 21 31 1 0 0 0 0 22 31 1 6 0 0 0 23 29 1 0 0 0 0 23 30 1 1 0 0 0 24 29 1 0 0 0 0 24 34 2 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 17 1 6 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 28 1 0 0 0 0 27 38 1 6 0 0 0 28 31 1 1 0 0 0 28 39 1 0 0 0 0 30 6 1 1 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.26
Volume:	557.1
LogP:	3.543
LogD:	2.614
LogS:	-4.519
# Rotatable Bonds:	9
TPSA:	109.11
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	5.204
Fsp3:	0.548
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:	-5.226
MDCK Permeability:	4.6689168812008575e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	80.8800277709961%
Volume Distribution (VD):	2.399
Pgp-substrate:	17.104969024658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.501
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.643
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	5.899
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.8
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.184
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.243
Carcinogencity:	0.321
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC34056

Natural Product ID:	NPC34056
*Common Name:**	Turraflorin A
IUPAC Name:	methyl 2-[(1R,2S)-2-[(1R,5R,6R,7R,7aS)-6,7-diacetyloxy-1-(furan-3-yl)-7a-methyl-4-methylidene-2,5,6,7-tetrahydro-1H-inden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:
Standard InCHIKey:	NCVYEYGQXPQYTC-YTJYDEETSA-N
Standard InCHI:	InChI=1S/C31H38O8/c1-17-21-9-10-22(20-12-14-37-16-20)31(21,7)28(39-19(3)33)27(38-18(2)32)26(17)30(6)13-11-24(34)29(4,5)23(30)15-25(35)36-8/h9,11-14,16,22-23,26-28H,1,10,15H2,2-8H3/t22-,23+,26-,27-,28+,30+,31-/m1/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@@]2(C(=CC[C@@H]2c2cocc2)C1=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386306
PubChem CID:	12150033
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15400.0	nM	PMID[450205]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[450205]
NPT176	Organism	Artemia salina	Artemia salina	mortality	<	50.0	%	PMID[450205]

☑ 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 NPC34056 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	334
0.1-0.2	1364
0.2-0.3	2984
0.3-0.4	6617
0.4-0.5	12048
0.5-0.6	8342
0.6-0.7	9480
0.7-0.8	1275
0.8-0.85	217
0.85-0.9	32
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC116717
0.9178	High Similarity	NPC291150
0.9172	High Similarity	NPC471001
0.911	High Similarity	NPC5180
0.9	High Similarity	NPC197137
0.8993	High Similarity	NPC92979
0.8966	High Similarity	NPC470999
0.8958	High Similarity	NPC199044
0.8958	High Similarity	NPC238843
0.8944	High Similarity	NPC56197
0.8904	High Similarity	NPC471174
0.8889	High Similarity	NPC80635
0.8874	High Similarity	NPC469847
0.8867	High Similarity	NPC155939
0.8867	High Similarity	NPC296807
0.8867	High Similarity	NPC141538
0.8859	High Similarity	NPC471002
0.8836	High Similarity	NPC471292
0.8792	High Similarity	NPC272590
0.8792	High Similarity	NPC471000
0.8784	High Similarity	NPC234494
0.8776	High Similarity	NPC216755
0.8776	High Similarity	NPC71821
0.875	High Similarity	NPC470118
0.8742	High Similarity	NPC471175
0.8733	High Similarity	NPC29695
0.8733	High Similarity	NPC322546
0.8733	High Similarity	NPC182427
0.8733	High Similarity	NPC246164
0.8733	High Similarity	NPC308205
0.8725	High Similarity	NPC156189
0.8701	High Similarity	NPC471166
0.8701	High Similarity	NPC471003
0.8701	High Similarity	NPC471167
0.8684	High Similarity	NPC175964
0.8684	High Similarity	NPC471169
0.8658	High Similarity	NPC329180
0.8658	High Similarity	NPC470791
0.8658	High Similarity	NPC470790
0.8649	High Similarity	NPC302987
0.8645	High Similarity	NPC471168
0.8618	High Similarity	NPC264943
0.8609	High Similarity	NPC470996
0.8609	High Similarity	NPC33938
0.8609	High Similarity	NPC472672
0.86	High Similarity	NPC469335
0.86	High Similarity	NPC159927
0.86	High Similarity	NPC470997
0.86	High Similarity	NPC196846
0.8553	High Similarity	NPC302054
0.8553	High Similarity	NPC253201
0.8543	High Similarity	NPC18135
0.8533	High Similarity	NPC472654
0.8523	High Similarity	NPC255414
0.8514	High Similarity	NPC185456
0.8506	High Similarity	NPC167142
0.8506	High Similarity	NPC470119
0.8506	High Similarity	NPC475066
0.8506	High Similarity	NPC214495
0.8506	High Similarity	NPC472283
0.8497	Intermediate Similarity	NPC25351
0.8487	Intermediate Similarity	NPC294511
0.8487	Intermediate Similarity	NPC121615
0.8462	Intermediate Similarity	NPC472668
0.8462	Intermediate Similarity	NPC470792
0.8462	Intermediate Similarity	NPC5741
0.8452	Intermediate Similarity	NPC475226
0.8452	Intermediate Similarity	NPC477403
0.8452	Intermediate Similarity	NPC472671
0.8442	Intermediate Similarity	NPC469485
0.8442	Intermediate Similarity	NPC204663
0.8438	Intermediate Similarity	NPC285227
0.8435	Intermediate Similarity	NPC121158
0.8431	Intermediate Similarity	NPC98206
0.8431	Intermediate Similarity	NPC34421
0.8431	Intermediate Similarity	NPC237259
0.8425	Intermediate Similarity	NPC148374
0.8411	Intermediate Similarity	NPC69647
0.8411	Intermediate Similarity	NPC125182
0.8408	Intermediate Similarity	NPC663
0.8408	Intermediate Similarity	NPC472669
0.8408	Intermediate Similarity	NPC292389
0.8408	Intermediate Similarity	NPC469338
0.8408	Intermediate Similarity	NPC224394
0.8397	Intermediate Similarity	NPC191828
0.8397	Intermediate Similarity	NPC477402
0.8397	Intermediate Similarity	NPC470789
0.8387	Intermediate Similarity	NPC173544
0.8387	Intermediate Similarity	NPC195954
0.8387	Intermediate Similarity	NPC195131
0.8387	Intermediate Similarity	NPC472778
0.8387	Intermediate Similarity	NPC88007
0.8387	Intermediate Similarity	NPC472777
0.8387	Intermediate Similarity	NPC472776
0.8377	Intermediate Similarity	NPC469336
0.8377	Intermediate Similarity	NPC469850
0.8366	Intermediate Similarity	NPC476201
0.8365	Intermediate Similarity	NPC476224
0.8365	Intermediate Similarity	NPC472764
0.8355	Intermediate Similarity	NPC228842
0.8355	Intermediate Similarity	NPC477404
0.8355	Intermediate Similarity	NPC196864
0.8354	Intermediate Similarity	NPC126984
0.8354	Intermediate Similarity	NPC27541
0.8354	Intermediate Similarity	NPC61967
0.8354	Intermediate Similarity	NPC62692
0.8354	Intermediate Similarity	NPC469849
0.8354	Intermediate Similarity	NPC276551
0.8354	Intermediate Similarity	NPC470940
0.8344	Intermediate Similarity	NPC472771
0.8344	Intermediate Similarity	NPC69028
0.8344	Intermediate Similarity	NPC197596
0.8344	Intermediate Similarity	NPC68848
0.8344	Intermediate Similarity	NPC471007
0.8333	Intermediate Similarity	NPC84349
0.8333	Intermediate Similarity	NPC474932
0.8333	Intermediate Similarity	NPC237155
0.8323	Intermediate Similarity	NPC60973
0.8322	Intermediate Similarity	NPC251865
0.8313	Intermediate Similarity	NPC472765
0.8313	Intermediate Similarity	NPC472766
0.8312	Intermediate Similarity	NPC178932
0.8302	Intermediate Similarity	NPC470875
0.8291	Intermediate Similarity	NPC14499
0.8291	Intermediate Similarity	NPC285567
0.8291	Intermediate Similarity	NPC472773
0.8291	Intermediate Similarity	NPC475039
0.8291	Intermediate Similarity	NPC476197
0.8291	Intermediate Similarity	NPC476035
0.8289	Intermediate Similarity	NPC470998
0.8286	Intermediate Similarity	NPC137570
0.828	Intermediate Similarity	NPC25255
0.828	Intermediate Similarity	NPC287559
0.828	Intermediate Similarity	NPC305016
0.8278	Intermediate Similarity	NPC470941
0.8278	Intermediate Similarity	NPC221809
0.8272	Intermediate Similarity	NPC469848
0.8269	Intermediate Similarity	NPC7059
0.8269	Intermediate Similarity	NPC194499
0.8269	Intermediate Similarity	NPC286722
0.8258	Intermediate Similarity	NPC476262
0.8255	Intermediate Similarity	NPC223415
0.8255	Intermediate Similarity	NPC470741
0.8252	Intermediate Similarity	NPC471817
0.825	Intermediate Similarity	NPC478179
0.825	Intermediate Similarity	NPC473753
0.825	Intermediate Similarity	NPC173516
0.825	Intermediate Similarity	NPC473766
0.8247	Intermediate Similarity	NPC75906
0.8247	Intermediate Similarity	NPC268905
0.8247	Intermediate Similarity	NPC84063
0.8239	Intermediate Similarity	NPC123088
0.8235	Intermediate Similarity	NPC46551
0.8235	Intermediate Similarity	NPC212257
0.8232	Intermediate Similarity	NPC478177
0.8231	Intermediate Similarity	NPC90953
0.8228	Intermediate Similarity	NPC329938
0.8228	Intermediate Similarity	NPC470939
0.8228	Intermediate Similarity	NPC472767
0.8228	Intermediate Similarity	NPC6326
0.8228	Intermediate Similarity	NPC193798
0.8228	Intermediate Similarity	NPC18986
0.8217	Intermediate Similarity	NPC307383
0.8217	Intermediate Similarity	NPC473473
0.8217	Intermediate Similarity	NPC475295
0.8207	Intermediate Similarity	NPC158525
0.8205	Intermediate Similarity	NPC263265
0.8205	Intermediate Similarity	NPC41880
0.8205	Intermediate Similarity	NPC209364
0.82	Intermediate Similarity	NPC142113
0.8199	Intermediate Similarity	NPC471397
0.8199	Intermediate Similarity	NPC327922
0.8194	Intermediate Similarity	NPC293253
0.8194	Intermediate Similarity	NPC471006
0.8187	Intermediate Similarity	NPC472670
0.8187	Intermediate Similarity	NPC121995
0.8187	Intermediate Similarity	NPC307781
0.8187	Intermediate Similarity	NPC475779
0.8182	Intermediate Similarity	NPC298190
0.8176	Intermediate Similarity	NPC283209
0.8176	Intermediate Similarity	NPC165218
0.8176	Intermediate Similarity	NPC67003
0.8176	Intermediate Similarity	NPC477405
0.8165	Intermediate Similarity	NPC8389
0.8158	Intermediate Similarity	NPC224418
0.8153	Intermediate Similarity	NPC472772
0.8151	Intermediate Similarity	NPC146872
0.8151	Intermediate Similarity	NPC46896
0.8148	Intermediate Similarity	NPC118086
0.8148	Intermediate Similarity	NPC470995
0.8146	Intermediate Similarity	NPC5676
0.8146	Intermediate Similarity	NPC56731
0.8143	Intermediate Similarity	NPC179354
0.8141	Intermediate Similarity	NPC44675
0.8141	Intermediate Similarity	NPC214541
0.8137	Intermediate Similarity	NPC472775
0.8137	Intermediate Similarity	NPC476861
0.8137	Intermediate Similarity	NPC270312
0.8137	Intermediate Similarity	NPC472774
0.8137	Intermediate Similarity	NPC476850

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 NPC34056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	942
0.2-0.3	1990
0.3-0.4	2644
0.4-0.5	2039
0.5-0.6	952
0.6-0.7	281
0.7-0.8	24
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
0.7937	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5761	Phase 2
0.7799	Intermediate Similarity	NPD5760	Phase 2
0.7738	Intermediate Similarity	NPD6765	Approved
0.7738	Intermediate Similarity	NPD6764	Approved
0.7719	Intermediate Similarity	NPD8434	Phase 2
0.7597	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD6784	Approved
0.7558	Intermediate Similarity	NPD6785	Approved
0.7197	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD919	Approved
0.7179	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6599	Discontinued
0.7101	Intermediate Similarity	NPD8127	Discontinued
0.7099	Intermediate Similarity	NPD920	Approved
0.7093	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1471	Phase 3
0.7063	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD1247	Approved
0.6994	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6832	Phase 2
0.6946	Remote Similarity	NPD7819	Suspended
0.6946	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5494	Approved
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6914	Remote Similarity	NPD6799	Approved
0.6913	Remote Similarity	NPD1608	Approved
0.6913	Remote Similarity	NPD3972	Approved
0.6909	Remote Similarity	NPD7458	Discontinued
0.6909	Remote Similarity	NPD3226	Approved
0.6899	Remote Similarity	NPD2796	Approved
0.6887	Remote Similarity	NPD3266	Approved
0.6887	Remote Similarity	NPD3267	Approved
0.6887	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1243	Approved
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6355	Discontinued
0.6839	Remote Similarity	NPD8032	Phase 2
0.6836	Remote Similarity	NPD6559	Discontinued
0.6835	Remote Similarity	NPD3748	Approved
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4110	Phase 3
0.6826	Remote Similarity	NPD7411	Suspended
0.6821	Remote Similarity	NPD3926	Phase 2
0.681	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3817	Phase 2
0.6802	Remote Similarity	NPD7199	Phase 2
0.6791	Remote Similarity	NPD4107	Approved
0.679	Remote Similarity	NPD3887	Approved
0.6786	Remote Similarity	NPD6801	Discontinued
0.6774	Remote Similarity	NPD3268	Approved
0.6765	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6808	Phase 2
0.675	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6002	Phase 3
0.675	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5763	Approved
0.675	Remote Similarity	NPD6005	Phase 3
0.675	Remote Similarity	NPD6004	Phase 3
0.675	Remote Similarity	NPD5762	Approved
0.6748	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2799	Discontinued
0.6724	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1778	Approved
0.6711	Remote Similarity	NPD1876	Approved
0.6705	Remote Similarity	NPD2163	Approved
0.669	Remote Similarity	NPD1241	Discontinued
0.6687	Remote Similarity	NPD1551	Phase 2
0.6687	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD4482	Phase 3
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5844	Phase 1
0.6646	Remote Similarity	NPD7236	Approved
0.6646	Remote Similarity	NPD2344	Approved
0.6644	Remote Similarity	NPD5585	Approved
0.6627	Remote Similarity	NPD6385	Approved
0.6627	Remote Similarity	NPD6386	Approved
0.6626	Remote Similarity	NPD3750	Approved
0.6623	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8404	Phase 2
0.661	Remote Similarity	NPD7799	Discontinued
0.661	Remote Similarity	NPD3818	Discontinued
0.6608	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5402	Approved
0.6591	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1934	Approved
0.6584	Remote Similarity	NPD2438	Suspended
0.6584	Remote Similarity	NPD6099	Approved
0.6584	Remote Similarity	NPD6100	Approved
0.6582	Remote Similarity	NPD4307	Phase 2
0.6568	Remote Similarity	NPD7028	Phase 2
0.6556	Remote Similarity	NPD7685	Pre-registration
0.6554	Remote Similarity	NPD7473	Discontinued
0.655	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7239	Suspended
0.6543	Remote Similarity	NPD2353	Approved
0.6543	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2346	Discontinued
0.6541	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1933	Approved
0.6532	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3749	Approved
0.6527	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7033	Discontinued
0.6516	Remote Similarity	NPD5647	Approved
0.6516	Remote Similarity	NPD2798	Approved
0.6512	Remote Similarity	NPD5353	Approved
0.6509	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1549	Phase 2
0.65	Remote Similarity	NPD6653	Approved
0.6497	Remote Similarity	NPD2403	Approved
0.6497	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2309	Approved
0.6484	Remote Similarity	NPD8312	Approved
0.6484	Remote Similarity	NPD8313	Approved
0.6483	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4967	Phase 2
0.6474	Remote Similarity	NPD4966	Approved
0.6474	Remote Similarity	NPD4965	Approved
0.6471	Remote Similarity	NPD4380	Phase 2
0.6467	Remote Similarity	NPD2533	Approved
0.6467	Remote Similarity	NPD2532	Approved
0.6467	Remote Similarity	NPD2534	Approved
0.6467	Remote Similarity	NPD9545	Approved
0.6463	Remote Similarity	NPD2800	Approved
0.6456	Remote Similarity	NPD2313	Discontinued
0.6456	Remote Similarity	NPD6798	Discontinued
0.6452	Remote Similarity	NPD2797	Approved
0.6444	Remote Similarity	NPD7074	Phase 3
0.6442	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD447	Suspended
0.6433	Remote Similarity	NPD6873	Phase 2
0.6429	Remote Similarity	NPD4359	Approved
0.6425	Remote Similarity	NPD7497	Discontinued
0.6424	Remote Similarity	NPD8166	Discontinued
0.6424	Remote Similarity	NPD7003	Approved
0.642	Remote Similarity	NPD4308	Phase 3
0.641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1019	Discontinued
0.6409	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6166	Phase 2
0.6404	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.64	Remote Similarity	NPD9092	Discovery
0.64	Remote Similarity	NPD6234	Discontinued
0.6398	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD37	Approved
0.6395	Remote Similarity	NPD6279	Approved
0.6395	Remote Similarity	NPD6280	Approved
0.6392	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7095	Approved
0.6389	Remote Similarity	NPD7054	Approved
0.6386	Remote Similarity	NPD2354	Approved
0.6384	Remote Similarity	NPD7315	Approved
0.6384	Remote Similarity	NPD6232	Discontinued
0.6379	Remote Similarity	NPD7768	Phase 2
0.6376	Remote Similarity	NPD7157	Approved
0.6375	Remote Similarity	NPD4140	Approved
0.6375	Remote Similarity	NPD3142	Approved
0.6375	Remote Similarity	NPD3140	Approved
0.6375	Remote Similarity	NPD2979	Phase 3
0.6373	Remote Similarity	NPD3057	Approved
0.6369	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3146	Approved
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD9494	Approved
0.6364	Remote Similarity	NPD9717	Approved
0.6358	Remote Similarity	NPD2801	Approved
0.6354	Remote Similarity	NPD7472	Approved
0.6352	Remote Similarity	NPD3764	Approved
0.6348	Remote Similarity	NPD5242	Approved
0.634	Remote Similarity	NPD3496	Discontinued
0.634	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7177	Discontinued
0.6325	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5327	Phase 3
0.6319	Remote Similarity	NPD1510	Phase 2
0.6316	Remote Similarity	NPD5691	Approved
0.6313	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD4870	Approved
0.6303	Remote Similarity	NPD4534	Discontinued
0.6303	Remote Similarity	NPD2897	Discontinued
0.6302	Remote Similarity	NPD8285	Discontinued
0.6299	Remote Similarity	NPD1281	Approved
0.6298	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1607	Approved
0.6296	Remote Similarity	NPD6651	Approved
0.629	Remote Similarity	NPD8150	Discontinued
0.6289	Remote Similarity	NPD2972	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