NPASS Compound

Structure

NPC34315 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 0.8027 2.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4080 1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6740 -2.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7472 -2.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4080 0.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6053 -3.7073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6053 0.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0133 -0.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8027 1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6053 0.9268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6053 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0133 -1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2106 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6053 -1.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4080 -1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8027 1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8027 -1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.7073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8027 -0.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2106 -1.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4080 -0.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8027 -0.4634 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 4.8159 -1.8537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2106 0.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6053 -2.7805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8027 2.3171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8027 -4.1707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8027 -1.3902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8027 -4.1707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6053 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 34 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 24 1 0 0 0 0 12 2 1 6 0 0 0 12 18 1 0 0 0 0 12 35 1 0 0 0 0 13 23 1 6 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 14 27 2 0 0 0 0 15 23 1 1 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 18 30 2 0 0 0 0 19 25 1 0 0 0 0 19 31 2 0 0 0 0 20 32 2 0 0 0 0 20 34 1 0 0 0 0 21 26 1 0 0 0 0 21 33 2 0 0 0 0 21 35 1 0 0 0 0 23 5 1 6 0 0 0 24 26 1 6 0 0 0 25 26 1 1 0 0 0 26 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.2
Volume:	484.683
LogP:	1.557
LogD:	0.651
LogS:	-4.443
# Rotatable Bonds:	2
TPSA:	141.11
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	5.548
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.398
MDCK Permeability:	0.00010376418504165486
Pgp-inhibitor:	0.866
Pgp-substrate:	0.526
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.6
30% Bioavailability (F30%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.402
Plasma Protein Binding (PPB):	48.804046630859375%
Volume Distribution (VD):	0.253
Pgp-substrate:	42.296226501464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.793

ADMET: Excretion

Clearance (CL):	4.845
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.839
AMES Toxicity:	0.914
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.67
Skin Sensitization:	0.633
Carcinogencity:	0.719
Eye Corrosion:	0.065
Eye Irritation:	0.286
Respiratory Toxicity:	0.863

Download Data

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

Natural Product: NPC34315

Natural Product ID:	NPC34315
*Common Name:**	Terretonin E
IUPAC Name:	methyl (2R,4aS,4bR,10S,10aR,10bR,12aS)-6,10-dihydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-9,10,10b,11-tetrahydronaphtho[1,2-h]isochromene-4a-carboxylate
Synonyms:	terretonin E
Standard InCHIKey:	DXIRTOQNEFGTAD-CRPRLYOESA-N
Standard InCHI:	InChI=1S/C26H32O9/c1-11-9-13-23(5)15(28)10-14(27)22(3,4)17(23)16(29)19(31)25(13,7)26(20(32)34-8)21(33)35-12(2)18(30)24(11,26)6/h12-13,15,28-29H,1,9-10H2,2-8H3/t12-,13-,15+,23+,24-,25+,26-/m1/s1
SMILES:	C=C1C[C@@H]2[C@@]3(C)[C@H](CC(=O)C(C)(C)C3=C(C(=O)[C@@]2(C)[C@]2(C(=O)OC)C(=O)O[C@H](C)C(=O)[C@@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558895
PubChem CID:	45273302
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719247]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	Mediterranean sponge Psammocinia sp.	coast of Israel	n.a.	PMID[21676619]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3900.0	nM	PMID[455230]

☑ 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 NPC34315 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	256
0.1-0.2	1648
0.2-0.3	4965
0.3-0.4	8445
0.4-0.5	12559
0.5-0.6	7854
0.6-0.7	4732
0.7-0.8	2102
0.8-0.85	120
0.85-0.9	12
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9057	High Similarity	NPC250018
0.8981	High Similarity	NPC193948
0.8952	High Similarity	NPC292588
0.8942	High Similarity	NPC275583
0.8692	High Similarity	NPC202524
0.8584	High Similarity	NPC17772
0.8571	High Similarity	NPC16081
0.8571	High Similarity	NPC173686
0.8509	High Similarity	NPC470777
0.8482	Intermediate Similarity	NPC323821
0.8482	Intermediate Similarity	NPC473798
0.8482	Intermediate Similarity	NPC268238
0.8482	Intermediate Similarity	NPC143268
0.8482	Intermediate Similarity	NPC45218
0.8476	Intermediate Similarity	NPC472972
0.844	Intermediate Similarity	NPC293850
0.8421	Intermediate Similarity	NPC297179
0.8407	Intermediate Similarity	NPC40632
0.8407	Intermediate Similarity	NPC328374
0.8407	Intermediate Similarity	NPC251236
0.8407	Intermediate Similarity	NPC96312
0.8393	Intermediate Similarity	NPC208998
0.8393	Intermediate Similarity	NPC7921
0.8378	Intermediate Similarity	NPC171888
0.8378	Intermediate Similarity	NPC146945
0.8376	Intermediate Similarity	NPC265557
0.8376	Intermediate Similarity	NPC105926
0.8376	Intermediate Similarity	NPC91693
0.8376	Intermediate Similarity	NPC18945
0.8362	Intermediate Similarity	NPC470921
0.8348	Intermediate Similarity	NPC472933
0.8333	Intermediate Similarity	NPC470854
0.8333	Intermediate Similarity	NPC474654
0.8333	Intermediate Similarity	NPC287343
0.8333	Intermediate Similarity	NPC97908
0.8333	Intermediate Similarity	NPC122033
0.8333	Intermediate Similarity	NPC472927
0.8319	Intermediate Similarity	NPC474906
0.8319	Intermediate Similarity	NPC18547
0.8318	Intermediate Similarity	NPC163249
0.8305	Intermediate Similarity	NPC476729
0.8305	Intermediate Similarity	NPC24651
0.8291	Intermediate Similarity	NPC312833
0.8261	Intermediate Similarity	NPC251310
0.8261	Intermediate Similarity	NPC21326
0.8246	Intermediate Similarity	NPC152199
0.8246	Intermediate Similarity	NPC235539
0.8246	Intermediate Similarity	NPC134869
0.8241	Intermediate Similarity	NPC282233
0.8241	Intermediate Similarity	NPC70967
0.8241	Intermediate Similarity	NPC95585
0.8241	Intermediate Similarity	NPC33973
0.823	Intermediate Similarity	NPC49451
0.823	Intermediate Similarity	NPC159333
0.822	Intermediate Similarity	NPC67251
0.8214	Intermediate Similarity	NPC115303
0.8198	Intermediate Similarity	NPC77947
0.8198	Intermediate Similarity	NPC286174
0.8198	Intermediate Similarity	NPC27814
0.8198	Intermediate Similarity	NPC470615
0.8182	Intermediate Similarity	NPC201908
0.8182	Intermediate Similarity	NPC176949
0.8174	Intermediate Similarity	NPC472934
0.8165	Intermediate Similarity	NPC216245
0.8165	Intermediate Similarity	NPC213366
0.8165	Intermediate Similarity	NPC474558
0.8165	Intermediate Similarity	NPC2436
0.8165	Intermediate Similarity	NPC98603
0.8165	Intermediate Similarity	NPC135854
0.8165	Intermediate Similarity	NPC470251
0.8142	Intermediate Similarity	NPC11252
0.8142	Intermediate Similarity	NPC289312
0.8136	Intermediate Similarity	NPC471965
0.8131	Intermediate Similarity	NPC104861
0.8125	Intermediate Similarity	NPC129689
0.8108	Intermediate Similarity	NPC154608
0.8108	Intermediate Similarity	NPC192813
0.8108	Intermediate Similarity	NPC277017
0.8108	Intermediate Similarity	NPC476479
0.8103	Intermediate Similarity	NPC204552
0.8103	Intermediate Similarity	NPC188667
0.8103	Intermediate Similarity	NPC470776
0.8095	Intermediate Similarity	NPC477438
0.8095	Intermediate Similarity	NPC477437
0.8091	Intermediate Similarity	NPC181357
0.8087	Intermediate Similarity	NPC207217
0.8073	Intermediate Similarity	NPC179208
0.8073	Intermediate Similarity	NPC216114
0.8073	Intermediate Similarity	NPC95899
0.807	Intermediate Similarity	NPC472929
0.807	Intermediate Similarity	NPC198539
0.807	Intermediate Similarity	NPC52634
0.807	Intermediate Similarity	NPC472926
0.807	Intermediate Similarity	NPC326264
0.8067	Intermediate Similarity	NPC262199
0.8067	Intermediate Similarity	NPC202666
0.8067	Intermediate Similarity	NPC471961
0.8067	Intermediate Similarity	NPC471964
0.8067	Intermediate Similarity	NPC14617
0.8056	Intermediate Similarity	NPC124211
0.8056	Intermediate Similarity	NPC236585
0.8053	Intermediate Similarity	NPC472928
0.8053	Intermediate Similarity	NPC201992
0.8051	Intermediate Similarity	NPC477046
0.8051	Intermediate Similarity	NPC470779
0.8051	Intermediate Similarity	NPC102822
0.8034	Intermediate Similarity	NPC319570
0.8018	Intermediate Similarity	NPC144854
0.8018	Intermediate Similarity	NPC3316
0.8017	Intermediate Similarity	NPC309433
0.8	Intermediate Similarity	NPC471962
0.8	Intermediate Similarity	NPC177820
0.8	Intermediate Similarity	NPC247315
0.8	Intermediate Similarity	NPC475036
0.8	Intermediate Similarity	NPC470922
0.8	Intermediate Similarity	NPC30188
0.8	Intermediate Similarity	NPC84928
0.8	Intermediate Similarity	NPC471963
0.8	Intermediate Similarity	NPC477439
0.8	Intermediate Similarity	NPC96268
0.8	Intermediate Similarity	NPC65523
0.7982	Intermediate Similarity	NPC53222
0.7966	Intermediate Similarity	NPC112038
0.7966	Intermediate Similarity	NPC107338
0.7966	Intermediate Similarity	NPC109607
0.7963	Intermediate Similarity	NPC157787
0.7963	Intermediate Similarity	NPC46761
0.7963	Intermediate Similarity	NPC88198
0.7951	Intermediate Similarity	NPC188291
0.7949	Intermediate Similarity	NPC286347
0.7944	Intermediate Similarity	NPC89225
0.7934	Intermediate Similarity	NPC285091
0.7934	Intermediate Similarity	NPC87662
0.7931	Intermediate Similarity	NPC474734
0.7931	Intermediate Similarity	NPC270958
0.7928	Intermediate Similarity	NPC51452
0.7928	Intermediate Similarity	NPC102352
0.7913	Intermediate Similarity	NPC51978
0.7913	Intermediate Similarity	NPC202889
0.7913	Intermediate Similarity	NPC474271
0.7909	Intermediate Similarity	NPC159442
0.7909	Intermediate Similarity	NPC478057
0.7909	Intermediate Similarity	NPC96217
0.7905	Intermediate Similarity	NPC477436
0.7905	Intermediate Similarity	NPC477435
0.7903	Intermediate Similarity	NPC254614
0.7903	Intermediate Similarity	NPC476193
0.7903	Intermediate Similarity	NPC100390
0.7899	Intermediate Similarity	NPC75417
0.7895	Intermediate Similarity	NPC43775
0.789	Intermediate Similarity	NPC52899
0.789	Intermediate Similarity	NPC163963
0.789	Intermediate Similarity	NPC289148
0.7881	Intermediate Similarity	NPC475171
0.7881	Intermediate Similarity	NPC469488
0.7881	Intermediate Similarity	NPC268958
0.7881	Intermediate Similarity	NPC258592
0.7881	Intermediate Similarity	NPC309780
0.7881	Intermediate Similarity	NPC39211
0.7881	Intermediate Similarity	NPC180550
0.7881	Intermediate Similarity	NPC475775
0.7881	Intermediate Similarity	NPC208381
0.7881	Intermediate Similarity	NPC214484
0.7881	Intermediate Similarity	NPC476529
0.7881	Intermediate Similarity	NPC473884
0.7881	Intermediate Similarity	NPC35405
0.7881	Intermediate Similarity	NPC469945
0.7881	Intermediate Similarity	NPC11551
0.7881	Intermediate Similarity	NPC472949
0.7881	Intermediate Similarity	NPC114441
0.7881	Intermediate Similarity	NPC157868
0.7881	Intermediate Similarity	NPC178548
0.7881	Intermediate Similarity	NPC127530
0.7881	Intermediate Similarity	NPC6377
0.7881	Intermediate Similarity	NPC476960
0.7876	Intermediate Similarity	NPC310546
0.7876	Intermediate Similarity	NPC304495
0.787	Intermediate Similarity	NPC474793
0.7869	Intermediate Similarity	NPC476008
0.7863	Intermediate Similarity	NPC473590
0.7863	Intermediate Similarity	NPC224121
0.7863	Intermediate Similarity	NPC176513
0.7863	Intermediate Similarity	NPC470775
0.7851	Intermediate Similarity	NPC473255
0.7851	Intermediate Similarity	NPC7850
0.7851	Intermediate Similarity	NPC469842
0.7851	Intermediate Similarity	NPC469841
0.7851	Intermediate Similarity	NPC6615
0.785	Intermediate Similarity	NPC223169
0.785	Intermediate Similarity	NPC167193
0.785	Intermediate Similarity	NPC472806
0.785	Intermediate Similarity	NPC98874
0.7845	Intermediate Similarity	NPC243354
0.7845	Intermediate Similarity	NPC247069
0.7845	Intermediate Similarity	NPC469877
0.7845	Intermediate Similarity	NPC470919
0.7843	Intermediate Similarity	NPC229717
0.7838	Intermediate Similarity	NPC202793
0.7838	Intermediate Similarity	NPC137657
0.7833	Intermediate Similarity	NPC162574

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 NPC34315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	1954
0.2-0.3	3773
0.3-0.4	1994
0.4-0.5	721
0.5-0.6	259
0.6-0.7	158
0.7-0.8	55
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
0.8067	Intermediate Similarity	NPD8328	Phase 3
0.8036	Intermediate Similarity	NPD6373	Approved
0.8036	Intermediate Similarity	NPD6372	Approved
0.7895	Intermediate Similarity	NPD6650	Approved
0.7895	Intermediate Similarity	NPD6649	Approved
0.7863	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD5739	Approved
0.7768	Intermediate Similarity	NPD6675	Approved
0.7768	Intermediate Similarity	NPD7128	Approved
0.7768	Intermediate Similarity	NPD6402	Approved
0.7667	Intermediate Similarity	NPD6319	Approved
0.7632	Intermediate Similarity	NPD6899	Approved
0.7632	Intermediate Similarity	NPD6881	Approved
0.7632	Intermediate Similarity	NPD7320	Approved
0.7615	Intermediate Similarity	NPD7902	Approved
0.7545	Intermediate Similarity	NPD5696	Approved
0.7544	Intermediate Similarity	NPD5701	Approved
0.7544	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD8297	Approved
0.7521	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7515	Phase 2
0.7455	Intermediate Similarity	NPD6083	Phase 2
0.7455	Intermediate Similarity	NPD6084	Phase 2
0.7436	Intermediate Similarity	NPD6847	Approved
0.7436	Intermediate Similarity	NPD6617	Approved
0.7436	Intermediate Similarity	NPD8130	Phase 1
0.7436	Intermediate Similarity	NPD6869	Approved
0.7419	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD6012	Approved
0.7414	Intermediate Similarity	NPD6014	Approved
0.7414	Intermediate Similarity	NPD6013	Approved
0.7414	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6399	Phase 3
0.7381	Intermediate Similarity	NPD7736	Approved
0.7377	Intermediate Similarity	NPD6059	Approved
0.7377	Intermediate Similarity	NPD6054	Approved
0.7364	Intermediate Similarity	NPD4697	Phase 3
0.736	Intermediate Similarity	NPD6616	Approved
0.7339	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7900	Approved
0.7328	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6011	Approved
0.7315	Intermediate Similarity	NPD6411	Approved
0.7302	Intermediate Similarity	NPD7078	Approved
0.7302	Intermediate Similarity	NPD8293	Discontinued
0.7288	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6370	Approved
0.7196	Intermediate Similarity	NPD6672	Approved
0.7196	Intermediate Similarity	NPD5737	Approved
0.7177	Intermediate Similarity	NPD6016	Approved
0.7177	Intermediate Similarity	NPD6015	Approved
0.7167	Intermediate Similarity	NPD4632	Approved
0.7155	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD4755	Approved
0.7131	Intermediate Similarity	NPD6009	Approved
0.7131	Intermediate Similarity	NPD7115	Discovery
0.713	Intermediate Similarity	NPD5328	Approved
0.713	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6101	Approved
0.713	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5988	Approved
0.7117	Intermediate Similarity	NPD5695	Phase 3
0.7103	Intermediate Similarity	NPD3573	Approved
0.7094	Intermediate Similarity	NPD6412	Phase 2
0.708	Intermediate Similarity	NPD7638	Approved
0.7063	Intermediate Similarity	NPD7604	Phase 2
0.7059	Intermediate Similarity	NPD4634	Approved
0.7054	Intermediate Similarity	NPD5221	Approved
0.7054	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5222	Approved
0.7049	Intermediate Similarity	NPD6274	Approved
0.7049	Intermediate Similarity	NPD6868	Approved
0.704	Intermediate Similarity	NPD5983	Phase 2
0.7027	Intermediate Similarity	NPD5282	Discontinued
0.7018	Intermediate Similarity	NPD5285	Approved
0.7018	Intermediate Similarity	NPD4700	Approved
0.7018	Intermediate Similarity	NPD5286	Approved
0.7018	Intermediate Similarity	NPD4696	Approved
0.7018	Intermediate Similarity	NPD7640	Approved
0.7018	Intermediate Similarity	NPD7639	Approved
0.7016	Intermediate Similarity	NPD7101	Approved
0.7016	Intermediate Similarity	NPD7100	Approved
0.7009	Intermediate Similarity	NPD3618	Phase 1
0.7	Intermediate Similarity	NPD6079	Approved
0.6991	Remote Similarity	NPD5173	Approved
0.6964	Remote Similarity	NPD5210	Approved
0.6964	Remote Similarity	NPD4629	Approved
0.6953	Remote Similarity	NPD6336	Discontinued
0.6947	Remote Similarity	NPD7260	Phase 2
0.6937	Remote Similarity	NPD5779	Approved
0.6937	Remote Similarity	NPD5778	Approved
0.6935	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD4695	Discontinued
0.6923	Remote Similarity	NPD7319	Approved
0.6917	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6909	Approved
0.6905	Remote Similarity	NPD6908	Approved
0.6897	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD5225	Approved
0.6897	Remote Similarity	NPD4633	Approved
0.6897	Remote Similarity	NPD5224	Approved
0.6891	Remote Similarity	NPD6686	Approved
0.6881	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4767	Approved
0.6864	Remote Similarity	NPD4768	Approved
0.6855	Remote Similarity	NPD6317	Approved
0.6852	Remote Similarity	NPD6409	Approved
0.6852	Remote Similarity	NPD7334	Approved
0.6852	Remote Similarity	NPD5330	Approved
0.6852	Remote Similarity	NPD6684	Approved
0.6852	Remote Similarity	NPD7146	Approved
0.6852	Remote Similarity	NPD7521	Approved
0.6847	Remote Similarity	NPD8035	Phase 2
0.6847	Remote Similarity	NPD8034	Phase 2
0.6846	Remote Similarity	NPD6033	Approved
0.6838	Remote Similarity	NPD5175	Approved
0.6838	Remote Similarity	NPD5174	Approved
0.6822	Remote Similarity	NPD4786	Approved
0.6822	Remote Similarity	NPD7507	Approved
0.6818	Remote Similarity	NPD6673	Approved
0.6818	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD6904	Approved
0.6818	Remote Similarity	NPD6080	Approved
0.681	Remote Similarity	NPD5223	Approved
0.68	Remote Similarity	NPD6313	Approved
0.68	Remote Similarity	NPD6314	Approved
0.6792	Remote Similarity	NPD3667	Approved
0.6783	Remote Similarity	NPD4225	Approved
0.678	Remote Similarity	NPD5141	Approved
0.6772	Remote Similarity	NPD6921	Approved
0.6767	Remote Similarity	NPD6845	Suspended
0.675	Remote Similarity	NPD4730	Approved
0.675	Remote Similarity	NPD4729	Approved
0.6727	Remote Similarity	NPD6903	Approved
0.6695	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5247	Approved
0.6639	Remote Similarity	NPD5251	Approved
0.6639	Remote Similarity	NPD5250	Approved
0.6639	Remote Similarity	NPD5248	Approved
0.6639	Remote Similarity	NPD5249	Phase 3
0.6612	Remote Similarity	NPD5128	Approved
0.661	Remote Similarity	NPD7632	Discontinued
0.6609	Remote Similarity	NPD7614	Phase 1
0.6606	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3617	Approved
0.6549	Remote Similarity	NPD5693	Phase 1
0.6549	Remote Similarity	NPD6050	Approved
0.6545	Remote Similarity	NPD6098	Approved
0.6545	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5279	Phase 3
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6333	Approved
0.6522	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6334	Approved
0.6512	Remote Similarity	NPD8513	Phase 3
0.6512	Remote Similarity	NPD8516	Approved
0.6512	Remote Similarity	NPD8517	Approved
0.6512	Remote Similarity	NPD8515	Approved
0.6491	Remote Similarity	NPD4202	Approved
0.6475	Remote Similarity	NPD5168	Approved
0.6466	Remote Similarity	NPD7732	Phase 3
0.646	Remote Similarity	NPD5692	Phase 3
0.646	Remote Similarity	NPD6698	Approved
0.646	Remote Similarity	NPD46	Approved
0.6455	Remote Similarity	NPD5329	Approved
0.6452	Remote Similarity	NPD5217	Approved
0.6452	Remote Similarity	NPD5216	Approved
0.6452	Remote Similarity	NPD5215	Approved
0.6404	Remote Similarity	NPD7983	Approved
0.6404	Remote Similarity	NPD7637	Suspended
0.6404	Remote Similarity	NPD5694	Approved
0.6393	Remote Similarity	NPD6614	Approved
0.6371	Remote Similarity	NPD5169	Approved
0.6371	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD3668	Phase 3
0.6364	Remote Similarity	NPD4197	Approved
0.6355	Remote Similarity	NPD7645	Phase 2
0.6349	Remote Similarity	NPD8133	Approved
0.6325	Remote Similarity	NPD7839	Suspended
0.632	Remote Similarity	NPD5127	Approved
0.6279	Remote Similarity	NPD7328	Approved
0.6279	Remote Similarity	NPD7327	Approved
0.6261	Remote Similarity	NPD5284	Approved
0.6261	Remote Similarity	NPD5281	Approved
0.626	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD8033	Approved
0.626	Remote Similarity	NPD7899	Clinical (unspecified phase)

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