NPASS Compound

Structure

NPC106644 OpenBabel07101719152D 24 28 0 0 1 0 0 0 0 0999 V2000 -4.2912 3.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 -0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1057 -1.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5699 1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9821 2.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9821 0.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1651 0.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4330 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 -1.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2990 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2912 -0.5101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 -1.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7990 1.1160 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 -1.7321 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 8 16 1 0 0 0 0 9 16 1 0 0 0 0 9 19 2 0 0 0 0 10 18 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 6 0 0 0 12 16 1 6 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 6 0 0 0 13 18 1 0 0 0 0 14 17 1 6 0 0 0 14 24 1 0 0 0 0 15 22 2 0 0 0 0 15 24 1 0 0 0 0 16 2 1 6 0 0 0 17 3 1 1 0 0 0 17 23 1 0 0 0 0 18 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	316.661
LogP:	0.77
LogD:	0.303
LogS:	-4.012
# Rotatable Bonds:	0
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	6.781
Fsp3:	0.611
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.239
MDCK Permeability:	1.8495415133656934e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.686

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.362
Plasma Protein Binding (PPB):	70.18673706054688%
Volume Distribution (VD):	1.582
Pgp-substrate:	26.719518661499023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	2.452
Half-life (T1/2):	0.499

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.765
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.71
Carcinogencity:	0.288
Eye Corrosion:	0.006
Eye Irritation:	0.018
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC106644

Natural Product ID:	NPC106644
*Common Name:**	Samaderins A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BHRGGWSNTHQGED-QNHMRRABSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-7-4-9(19)16(2)8(7)5-10(20)18-6-23-17(3)13(18)15(22)24-14(17)11(21)12(16)18/h4-5,11-14,21H,6H2,1-3H3/t11-,12-,13+,14+,16-,17+,18-/m1/s1
SMILES:	O=C1O[C@@H]2[C@@]3([C@H]1[C@]1(CO3)C(=O)C=C3[C@]([C@H]1[C@H]2O)(C)C(=O)C=C3C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2270648
PubChem CID:	441807
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO29535	Samadera indica	Species	Simaroubaceae	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
Others	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	7.4	%	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	211.2	hr	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	362.4	hr	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	115.2	hr	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	86.4	hr	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	69.6	hr	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	21.1	%	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	16.2	%	PMID[525257]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	18.9	%	PMID[525257]

☑ 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 NPC106644 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	241
0.1-0.2	1235
0.2-0.3	4572
0.3-0.4	7939
0.4-0.5	12835
0.5-0.6	8041
0.6-0.7	6316
0.7-0.8	1471
0.8-0.85	42
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC153239
0.8938	High Similarity	NPC207217
0.8818	High Similarity	NPC19412
0.8684	High Similarity	NPC117712
0.8496	Intermediate Similarity	NPC210005
0.8468	Intermediate Similarity	NPC102352
0.8462	Intermediate Similarity	NPC17772
0.8421	Intermediate Similarity	NPC188738
0.8376	Intermediate Similarity	NPC53396
0.8376	Intermediate Similarity	NPC474654
0.8376	Intermediate Similarity	NPC287343
0.8376	Intermediate Similarity	NPC98249
0.8376	Intermediate Similarity	NPC97908
0.8376	Intermediate Similarity	NPC122033
0.8376	Intermediate Similarity	NPC470854
0.8348	Intermediate Similarity	NPC472002
0.8319	Intermediate Similarity	NPC154608
0.8319	Intermediate Similarity	NPC192813
0.8319	Intermediate Similarity	NPC277017
0.8305	Intermediate Similarity	NPC284707
0.8276	Intermediate Similarity	NPC49451
0.8264	Intermediate Similarity	NPC471392
0.8235	Intermediate Similarity	NPC470777
0.823	Intermediate Similarity	NPC3316
0.823	Intermediate Similarity	NPC144854
0.8211	Intermediate Similarity	NPC476008
0.8205	Intermediate Similarity	NPC143268
0.8205	Intermediate Similarity	NPC323821
0.8205	Intermediate Similarity	NPC45218
0.8205	Intermediate Similarity	NPC268238
0.819	Intermediate Similarity	NPC474516
0.8182	Intermediate Similarity	NPC312833
0.8174	Intermediate Similarity	NPC286880
0.8174	Intermediate Similarity	NPC474567
0.8158	Intermediate Similarity	NPC29827
0.8151	Intermediate Similarity	NPC204552
0.8151	Intermediate Similarity	NPC188667
0.8142	Intermediate Similarity	NPC181357
0.8136	Intermediate Similarity	NPC16081
0.8136	Intermediate Similarity	NPC40632
0.8136	Intermediate Similarity	NPC328374
0.8136	Intermediate Similarity	NPC251236
0.8136	Intermediate Similarity	NPC173686
0.8136	Intermediate Similarity	NPC96312
0.813	Intermediate Similarity	NPC477745
0.8125	Intermediate Similarity	NPC243014
0.812	Intermediate Similarity	NPC208998
0.812	Intermediate Similarity	NPC194273
0.812	Intermediate Similarity	NPC471204
0.812	Intermediate Similarity	NPC7921
0.812	Intermediate Similarity	NPC52634
0.8115	Intermediate Similarity	NPC91693
0.8115	Intermediate Similarity	NPC18945
0.8115	Intermediate Similarity	NPC105926
0.8115	Intermediate Similarity	NPC265557
0.8103	Intermediate Similarity	NPC171888
0.8103	Intermediate Similarity	NPC474229
0.8103	Intermediate Similarity	NPC146945
0.8099	Intermediate Similarity	NPC477046
0.8099	Intermediate Similarity	NPC470921
0.8099	Intermediate Similarity	NPC102822
0.8095	Intermediate Similarity	NPC102316
0.808	Intermediate Similarity	NPC264192
0.807	Intermediate Similarity	NPC230541
0.807	Intermediate Similarity	NPC59530
0.8067	Intermediate Similarity	NPC469684
0.8053	Intermediate Similarity	NPC65523
0.8053	Intermediate Similarity	NPC471293
0.8051	Intermediate Similarity	NPC473898
0.8051	Intermediate Similarity	NPC473798
0.8051	Intermediate Similarity	NPC243354
0.8049	Intermediate Similarity	NPC476729
0.8049	Intermediate Similarity	NPC24651
0.8034	Intermediate Similarity	NPC205534
0.8031	Intermediate Similarity	NPC168879
0.8017	Intermediate Similarity	NPC5284
0.8017	Intermediate Similarity	NPC112038
0.8017	Intermediate Similarity	NPC109973
0.8	Intermediate Similarity	NPC297179
0.8	Intermediate Similarity	NPC470776
0.8	Intermediate Similarity	NPC251310
0.8	Intermediate Similarity	NPC188291
0.8	Intermediate Similarity	NPC473888
0.7984	Intermediate Similarity	NPC181999
0.7983	Intermediate Similarity	NPC270478
0.7983	Intermediate Similarity	NPC266728
0.7983	Intermediate Similarity	NPC49492
0.7982	Intermediate Similarity	NPC471332
0.7982	Intermediate Similarity	NPC471333
0.7982	Intermediate Similarity	NPC472655
0.7969	Intermediate Similarity	NPC242486
0.7969	Intermediate Similarity	NPC15215
0.7967	Intermediate Similarity	NPC67251
0.7966	Intermediate Similarity	NPC320118
0.7966	Intermediate Similarity	NPC478212
0.7966	Intermediate Similarity	NPC470120
0.7966	Intermediate Similarity	NPC474271
0.7953	Intermediate Similarity	NPC100390
0.7953	Intermediate Similarity	NPC254614
0.7951	Intermediate Similarity	NPC470779
0.7949	Intermediate Similarity	NPC471243
0.7949	Intermediate Similarity	NPC201992
0.7934	Intermediate Similarity	NPC469488
0.7931	Intermediate Similarity	NPC310546
0.7931	Intermediate Similarity	NPC141350
0.7917	Intermediate Similarity	NPC478204
0.7917	Intermediate Similarity	NPC58662
0.7917	Intermediate Similarity	NPC475323
0.7917	Intermediate Similarity	NPC284068
0.7917	Intermediate Similarity	NPC473656
0.7917	Intermediate Similarity	NPC176513
0.7917	Intermediate Similarity	NPC470775
0.7913	Intermediate Similarity	NPC166993
0.7899	Intermediate Similarity	NPC326542
0.7899	Intermediate Similarity	NPC472400
0.7899	Intermediate Similarity	NPC299849
0.7886	Intermediate Similarity	NPC222688
0.7881	Intermediate Similarity	NPC289312
0.7881	Intermediate Similarity	NPC234042
0.7881	Intermediate Similarity	NPC269530
0.7881	Intermediate Similarity	NPC11252
0.7881	Intermediate Similarity	NPC207251
0.7881	Intermediate Similarity	NPC152117
0.7881	Intermediate Similarity	NPC476801
0.7869	Intermediate Similarity	NPC475885
0.7869	Intermediate Similarity	NPC472004
0.7857	Intermediate Similarity	NPC477656
0.7857	Intermediate Similarity	NPC477655
0.7851	Intermediate Similarity	NPC478205
0.7851	Intermediate Similarity	NPC108581
0.7851	Intermediate Similarity	NPC478206
0.7845	Intermediate Similarity	NPC273155
0.7845	Intermediate Similarity	NPC293850
0.784	Intermediate Similarity	NPC47113
0.784	Intermediate Similarity	NPC293112
0.784	Intermediate Similarity	NPC174367
0.7833	Intermediate Similarity	NPC152199
0.7833	Intermediate Similarity	NPC213084
0.7833	Intermediate Similarity	NPC134869
0.7833	Intermediate Similarity	NPC235539
0.7833	Intermediate Similarity	NPC190185
0.7833	Intermediate Similarity	NPC179626
0.7833	Intermediate Similarity	NPC106228
0.7833	Intermediate Similarity	NPC138372
0.7826	Intermediate Similarity	NPC200957
0.7826	Intermediate Similarity	NPC96377
0.7826	Intermediate Similarity	NPC138908
0.7826	Intermediate Similarity	NPC222833
0.7826	Intermediate Similarity	NPC469607
0.7823	Intermediate Similarity	NPC11895
0.7815	Intermediate Similarity	NPC194100
0.7815	Intermediate Similarity	NPC9848
0.7815	Intermediate Similarity	NPC312017
0.7815	Intermediate Similarity	NPC469463
0.7815	Intermediate Similarity	NPC469454
0.7815	Intermediate Similarity	NPC469496
0.7815	Intermediate Similarity	NPC51978
0.7815	Intermediate Similarity	NPC250109
0.7815	Intermediate Similarity	NPC472757
0.7815	Intermediate Similarity	NPC198539
0.7815	Intermediate Similarity	NPC962
0.7812	Intermediate Similarity	NPC33378
0.7812	Intermediate Similarity	NPC254146
0.7812	Intermediate Similarity	NPC6274
0.7807	Intermediate Similarity	NPC471005
0.7807	Intermediate Similarity	NPC277074
0.7807	Intermediate Similarity	NPC159442
0.7807	Intermediate Similarity	NPC209298
0.7805	Intermediate Similarity	NPC471999
0.7805	Intermediate Similarity	NPC472401
0.7805	Intermediate Similarity	NPC472000
0.7805	Intermediate Similarity	NPC310511
0.7797	Intermediate Similarity	NPC469655
0.7797	Intermediate Similarity	NPC179798
0.7797	Intermediate Similarity	NPC469656
0.7797	Intermediate Similarity	NPC474846
0.7797	Intermediate Similarity	NPC304180
0.7795	Intermediate Similarity	NPC231529
0.7788	Intermediate Similarity	NPC101067
0.7788	Intermediate Similarity	NPC476134
0.7787	Intermediate Similarity	NPC268958
0.7787	Intermediate Similarity	NPC236918
0.7787	Intermediate Similarity	NPC470186
0.7787	Intermediate Similarity	NPC156745
0.7787	Intermediate Similarity	NPC230513
0.7787	Intermediate Similarity	NPC312536
0.7769	Intermediate Similarity	NPC218970
0.7769	Intermediate Similarity	NPC156252
0.776	Intermediate Similarity	NPC8369
0.776	Intermediate Similarity	NPC473255
0.7759	Intermediate Similarity	NPC220974
0.7759	Intermediate Similarity	NPC473037
0.7759	Intermediate Similarity	NPC133422
0.775	Intermediate Similarity	NPC474906
0.775	Intermediate Similarity	NPC18547
0.7742	Intermediate Similarity	NPC287236
0.7742	Intermediate Similarity	NPC269642
0.7742	Intermediate Similarity	NPC19464
0.7742	Intermediate Similarity	NPC170538
0.7739	Intermediate Similarity	NPC470104

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 NPC106644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1594
0.2-0.3	3949
0.3-0.4	2232
0.4-0.5	676
0.5-0.6	274
0.6-0.7	175
0.7-0.8	42
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
0.7724	Intermediate Similarity	NPD6319	Approved
0.7638	Intermediate Similarity	NPD7078	Approved
0.7619	Intermediate Similarity	NPD7492	Approved
0.7581	Intermediate Similarity	NPD6054	Approved
0.7581	Intermediate Similarity	NPD6059	Approved
0.7559	Intermediate Similarity	NPD6616	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD6008	Approved
0.752	Intermediate Similarity	NPD6016	Approved
0.752	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD6373	Approved
0.7479	Intermediate Similarity	NPD6372	Approved
0.746	Intermediate Similarity	NPD5988	Approved
0.746	Intermediate Similarity	NPD6370	Approved
0.7442	Intermediate Similarity	NPD7736	Approved
0.7395	Intermediate Similarity	NPD7320	Approved
0.7395	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6675	Approved
0.7373	Intermediate Similarity	NPD7128	Approved
0.7373	Intermediate Similarity	NPD6402	Approved
0.7373	Intermediate Similarity	NPD5739	Approved
0.7355	Intermediate Similarity	NPD6649	Approved
0.7355	Intermediate Similarity	NPD6650	Approved
0.7333	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5697	Approved
0.7311	Intermediate Similarity	NPD5701	Approved
0.7295	Intermediate Similarity	NPD8297	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD8328	Phase 3
0.7252	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.725	Intermediate Similarity	NPD6881	Approved
0.72	Intermediate Similarity	NPD6009	Approved
0.72	Intermediate Similarity	NPD7115	Discovery
0.719	Intermediate Similarity	NPD6013	Approved
0.719	Intermediate Similarity	NPD6012	Approved
0.719	Intermediate Similarity	NPD6014	Approved
0.7155	Intermediate Similarity	NPD4225	Approved
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7109	Intermediate Similarity	NPD5983	Phase 2
0.7107	Intermediate Similarity	NPD6011	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7073	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD8130	Phase 1
0.7073	Intermediate Similarity	NPD6617	Approved
0.7069	Intermediate Similarity	NPD4755	Approved
0.7069	Intermediate Similarity	NPD7902	Approved
0.7049	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6033	Approved
0.7025	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7507	Approved
0.7018	Intermediate Similarity	NPD6399	Phase 3
0.7016	Intermediate Similarity	NPD6882	Approved
0.7009	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD7604	Phase 2
0.6983	Remote Similarity	NPD4697	Phase 3
0.6957	Remote Similarity	NPD5282	Discontinued
0.6949	Remote Similarity	NPD4700	Approved
0.6949	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD4696	Approved
0.6949	Remote Similarity	NPD5286	Approved
0.6935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6411	Approved
0.6903	Remote Similarity	NPD5328	Approved
0.6897	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD1700	Approved
0.6885	Remote Similarity	NPD6412	Phase 2
0.687	Remote Similarity	NPD5778	Approved
0.687	Remote Similarity	NPD5779	Approved
0.6855	Remote Similarity	NPD6371	Approved
0.685	Remote Similarity	NPD6274	Approved
0.6846	Remote Similarity	NPD8517	Approved
0.6846	Remote Similarity	NPD8513	Phase 3
0.6846	Remote Similarity	NPD8516	Approved
0.6846	Remote Similarity	NPD8515	Approved
0.6846	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5224	Approved
0.6833	Remote Similarity	NPD5226	Approved
0.6833	Remote Similarity	NPD4633	Approved
0.6833	Remote Similarity	NPD5225	Approved
0.6833	Remote Similarity	NPD5211	Phase 2
0.681	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7900	Approved
0.681	Remote Similarity	NPD7748	Approved
0.6797	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3618	Phase 1
0.6783	Remote Similarity	NPD5284	Approved
0.6783	Remote Similarity	NPD5281	Approved
0.6783	Remote Similarity	NPD7515	Phase 2
0.6783	Remote Similarity	NPD6079	Approved
0.678	Remote Similarity	NPD6083	Phase 2
0.678	Remote Similarity	NPD6084	Phase 2
0.6777	Remote Similarity	NPD5175	Approved
0.6777	Remote Similarity	NPD5174	Approved
0.6754	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6101	Approved
0.6752	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5695	Phase 3
0.675	Remote Similarity	NPD5223	Approved
0.6724	Remote Similarity	NPD4202	Approved
0.6723	Remote Similarity	NPD7638	Approved
0.6721	Remote Similarity	NPD5141	Approved
0.6718	Remote Similarity	NPD6921	Approved
0.6696	Remote Similarity	NPD5207	Approved
0.6695	Remote Similarity	NPD5221	Approved
0.6695	Remote Similarity	NPD5222	Approved
0.6695	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6686	Approved
0.6692	Remote Similarity	NPD7516	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6639	Remote Similarity	NPD5173	Approved
0.6639	Remote Similarity	NPD4754	Approved
0.6638	Remote Similarity	NPD7983	Approved
0.6615	Remote Similarity	NPD7328	Approved
0.6615	Remote Similarity	NPD6314	Approved
0.6615	Remote Similarity	NPD7327	Approved
0.6615	Remote Similarity	NPD6335	Approved
0.6615	Remote Similarity	NPD6313	Approved
0.6614	Remote Similarity	NPD6053	Discontinued
0.6613	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4629	Approved
0.661	Remote Similarity	NPD5210	Approved
0.6593	Remote Similarity	NPD8074	Phase 3
0.6591	Remote Similarity	NPD6908	Approved
0.6591	Remote Similarity	NPD6909	Approved
0.6579	Remote Similarity	NPD3573	Approved
0.656	Remote Similarity	NPD4730	Approved
0.656	Remote Similarity	NPD4729	Approved
0.656	Remote Similarity	NPD5128	Approved
0.6525	Remote Similarity	NPD6001	Approved
0.6522	Remote Similarity	NPD7260	Phase 2
0.6496	Remote Similarity	NPD8034	Phase 2
0.6496	Remote Similarity	NPD8035	Phase 2
0.6496	Remote Similarity	NPD7637	Suspended
0.6493	Remote Similarity	NPD6067	Discontinued
0.6491	Remote Similarity	NPD5279	Phase 3
0.6491	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6845	Suspended
0.6475	Remote Similarity	NPD5344	Discontinued
0.6466	Remote Similarity	NPD8380	Approved
0.6466	Remote Similarity	NPD4753	Phase 2
0.6466	Remote Similarity	NPD8296	Approved
0.6466	Remote Similarity	NPD8335	Approved
0.6466	Remote Similarity	NPD7503	Approved
0.6466	Remote Similarity	NPD8378	Approved
0.6466	Remote Similarity	NPD8379	Approved
0.6462	Remote Similarity	NPD6868	Approved
0.6457	Remote Similarity	NPD5249	Phase 3
0.6457	Remote Similarity	NPD5248	Approved
0.6457	Remote Similarity	NPD5250	Approved
0.6457	Remote Similarity	NPD5247	Approved
0.6457	Remote Similarity	NPD5251	Approved
0.6449	Remote Similarity	NPD5956	Approved
0.6435	Remote Similarity	NPD7524	Approved
0.641	Remote Similarity	NPD5692	Phase 3
0.6406	Remote Similarity	NPD5215	Approved
0.6406	Remote Similarity	NPD5217	Approved
0.6406	Remote Similarity	NPD5216	Approved
0.6404	Remote Similarity	NPD1694	Approved
0.6393	Remote Similarity	NPD6648	Approved
0.6391	Remote Similarity	NPD8294	Approved
0.6391	Remote Similarity	NPD8377	Approved
0.6379	Remote Similarity	NPD6672	Approved
0.6379	Remote Similarity	NPD5737	Approved
0.6379	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD6334	Approved
0.6364	Remote Similarity	NPD6333	Approved
0.6357	Remote Similarity	NPD8338	Approved
0.6356	Remote Similarity	NPD5694	Approved
0.6356	Remote Similarity	NPD6050	Approved
0.6348	Remote Similarity	NPD7334	Approved
0.6348	Remote Similarity	NPD7146	Approved
0.6348	Remote Similarity	NPD6684	Approved
0.6348	Remote Similarity	NPD5330	Approved
0.6348	Remote Similarity	NPD7521	Approved
0.6348	Remote Similarity	NPD6409	Approved
0.6343	Remote Similarity	NPD8033	Approved
0.6328	Remote Similarity	NPD5135	Approved
0.6328	Remote Similarity	NPD5169	Approved
0.6328	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD4786	Approved
0.6308	Remote Similarity	NPD8133	Approved
0.6294	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD3667	Approved
0.6279	Remote Similarity	NPD5127	Approved
0.6271	Remote Similarity	NPD6698	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