NPASS Compound

Structure

CID269677 OpenBabel06191716072D 33 34 0 0 1 0 0 0 0 0999 V2000 -0.3575 -9.0744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9885 -10.1644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8014 -5.0322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7263 -2.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9644 -0.3734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3955 2.8605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9011 -7.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1740 -4.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2491 -1.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2595 -8.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5304 -6.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1844 -5.6530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4553 -3.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8907 -2.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6198 -1.1415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6302 -9.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1721 -5.8094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0970 -3.0087 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 1.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 3.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8955 1.9945 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 20 1 0 0 0 0 2 20 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 28 1 0 0 0 0 9 12 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 16 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 25 30 2 0 0 0 0 26 29 1 0 0 0 0 26 31 2 0 0 0 0 27 7 1 1 0 0 0 27 33 1 0 0 0 0 28 29 1 6 0 0 0 28 32 1 0 0 0 0 29 19 1 1 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.37
Volume:	520.279
LogP:	7.356
LogD:	6.676
LogS:	-5.629
# Rotatable Bonds:	12
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	4.973
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.764
MDCK Permeability:	1.5900674043223262e-05
Pgp-inhibitor:	0.874
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.429

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	98.18685150146484%
Volume Distribution (VD):	1.853
Pgp-substrate:	3.153789520263672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.458
CYP2C19-inhibitor:	0.789
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.811
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.751
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.833

ADMET: Excretion

Clearance (CL):	5.076
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.931
Carcinogencity:	0.035
Eye Corrosion:	0.004
Eye Irritation:	0.072
Respiratory Toxicity:	0.127

Download Data

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

Natural Product: NPC269677

Natural Product ID:	NPC269677
*Common Name:**	XSELOQGXDYVVCH-CYDJTLQWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XSELOQGXDYVVCH-CYDJTLQWSA-N
Standard InCHI:	InChI=1S/C29H50O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-27(7)18-19-29(33-27)26(31)24(6)23(5)25(30)28(29,8)32/h20-22,32H,9-19H2,1-8H3/t21-,22-,27-,28+,29+/m1/s1
SMILES:	C[C@H](CCC[C@@H](CCCC(C)C)C)CCC[C@]1(C)CC[C@]2(O1)C(=O)C(=C(C(=O)[C@]2(C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3356398
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23548547]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25497963]
NPO13501	Gynura segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13501	Gynura segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13501	Gynura segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13501	Gynura segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	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	3
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	Inhibition	<	50.0	%	PMID[490819]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	11010.0	nM	PMID[490819]
NPT205	Individual Protein	Protein-tyrosine phosphatase 1C	Homo sapiens	Inhibition	<	50.0	%	PMID[490819]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Inhibition	<	50.0	%	PMID[490819]
NPT1870	Individual Protein	Receptor-type tyrosine-protein phosphatase F (LAR)	Homo sapiens	Inhibition	<	50.0	%	PMID[490819]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	13.85	%	PMID[490819]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[490819]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	Inhibition	<	50.0	%	PMID[490819]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[490819]

☑ 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 NPC269677 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	203
0.1-0.2	1627
0.2-0.3	6718
0.3-0.4	13765
0.4-0.5	11374
0.5-0.6	6783
0.6-0.7	2087
0.7-0.8	137
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8352	Intermediate Similarity	NPC144629
0.7732	Intermediate Similarity	NPC27105
0.7653	Intermediate Similarity	NPC203388
0.7653	Intermediate Similarity	NPC99657
0.7653	Intermediate Similarity	NPC471330
0.7653	Intermediate Similarity	NPC472687
0.7653	Intermediate Similarity	NPC471331
0.764	Intermediate Similarity	NPC474353
0.7604	Intermediate Similarity	NPC114162
0.7604	Intermediate Similarity	NPC469819
0.7573	Intermediate Similarity	NPC29827
0.7528	Intermediate Similarity	NPC472948
0.75	Intermediate Similarity	NPC61275
0.75	Intermediate Similarity	NPC181645
0.7477	Intermediate Similarity	NPC247069
0.7449	Intermediate Similarity	NPC472734
0.7449	Intermediate Similarity	NPC8803
0.7449	Intermediate Similarity	NPC272411
0.7449	Intermediate Similarity	NPC472733
0.7447	Intermediate Similarity	NPC476708
0.7431	Intermediate Similarity	NPC297179
0.7423	Intermediate Similarity	NPC477439
0.7407	Intermediate Similarity	NPC16081
0.7407	Intermediate Similarity	NPC207217
0.7407	Intermediate Similarity	NPC173686
0.7404	Intermediate Similarity	NPC154608
0.7404	Intermediate Similarity	NPC277017
0.7404	Intermediate Similarity	NPC192813
0.7396	Intermediate Similarity	NPC248913
0.7396	Intermediate Similarity	NPC146852
0.7396	Intermediate Similarity	NPC111883
0.7379	Intermediate Similarity	NPC471333
0.7379	Intermediate Similarity	NPC471332
0.7379	Intermediate Similarity	NPC181357
0.7374	Intermediate Similarity	NPC472732
0.7374	Intermediate Similarity	NPC472731
0.7347	Intermediate Similarity	NPC200702
0.7347	Intermediate Similarity	NPC477437
0.7347	Intermediate Similarity	NPC477438
0.734	Intermediate Similarity	NPC197333
0.7333	Intermediate Similarity	NPC87335
0.7333	Intermediate Similarity	NPC101018
0.7327	Intermediate Similarity	NPC475867
0.7327	Intermediate Similarity	NPC270155
0.7327	Intermediate Similarity	NPC472753
0.732	Intermediate Similarity	NPC477436
0.732	Intermediate Similarity	NPC477435
0.7317	Intermediate Similarity	NPC61473
0.7315	Intermediate Similarity	NPC323821
0.7315	Intermediate Similarity	NPC45218
0.7315	Intermediate Similarity	NPC143268
0.7315	Intermediate Similarity	NPC268238
0.7308	Intermediate Similarity	NPC3316
0.7308	Intermediate Similarity	NPC473165
0.7308	Intermediate Similarity	NPC144854
0.7308	Intermediate Similarity	NPC202524
0.73	Intermediate Similarity	NPC470541
0.73	Intermediate Similarity	NPC472730
0.73	Intermediate Similarity	NPC153776
0.73	Intermediate Similarity	NPC472729
0.73	Intermediate Similarity	NPC177680
0.7297	Intermediate Similarity	NPC478051
0.729	Intermediate Similarity	NPC193948
0.7282	Intermediate Similarity	NPC40170
0.7282	Intermediate Similarity	NPC65523
0.7282	Intermediate Similarity	NPC13385
0.7273	Intermediate Similarity	NPC239758
0.7273	Intermediate Similarity	NPC93271
0.7273	Intermediate Similarity	NPC135576
0.7273	Intermediate Similarity	NPC17772
0.7264	Intermediate Similarity	NPC210005
0.7263	Intermediate Similarity	NPC476707
0.7263	Intermediate Similarity	NPC476706
0.7263	Intermediate Similarity	NPC475001
0.7263	Intermediate Similarity	NPC185059
0.7255	Intermediate Similarity	NPC80781
0.7255	Intermediate Similarity	NPC472754
0.7255	Intermediate Similarity	NPC39996
0.7255	Intermediate Similarity	NPC478176
0.7248	Intermediate Similarity	NPC96312
0.7248	Intermediate Similarity	NPC251236
0.7248	Intermediate Similarity	NPC40632
0.7248	Intermediate Similarity	NPC235539
0.7248	Intermediate Similarity	NPC134869
0.7248	Intermediate Similarity	NPC328374
0.7248	Intermediate Similarity	NPC152199
0.7245	Intermediate Similarity	NPC212812
0.7228	Intermediate Similarity	NPC472972
0.7228	Intermediate Similarity	NPC472728
0.7228	Intermediate Similarity	NPC472727
0.7228	Intermediate Similarity	NPC474802
0.7212	Intermediate Similarity	NPC292588
0.7212	Intermediate Similarity	NPC102352
0.7207	Intermediate Similarity	NPC470777
0.72	Intermediate Similarity	NPC20078
0.72	Intermediate Similarity	NPC473574
0.7184	Intermediate Similarity	NPC131366
0.7184	Intermediate Similarity	NPC475873
0.7184	Intermediate Similarity	NPC474330
0.7184	Intermediate Similarity	NPC472755
0.7184	Intermediate Similarity	NPC474207
0.7182	Intermediate Similarity	NPC470854
0.7182	Intermediate Similarity	NPC287343
0.7182	Intermediate Similarity	NPC97908
0.7182	Intermediate Similarity	NPC122033
0.7182	Intermediate Similarity	NPC474654
0.7157	Intermediate Similarity	NPC474742
0.7157	Intermediate Similarity	NPC124211
0.7157	Intermediate Similarity	NPC476134
0.7157	Intermediate Similarity	NPC472702
0.7157	Intermediate Similarity	NPC472685
0.7157	Intermediate Similarity	NPC101067
0.7156	Intermediate Similarity	NPC18547
0.7156	Intermediate Similarity	NPC473798
0.7156	Intermediate Similarity	NPC474906
0.713	Intermediate Similarity	NPC474516
0.713	Intermediate Similarity	NPC269530
0.7128	Intermediate Similarity	NPC79573
0.7117	Intermediate Similarity	NPC204552
0.7117	Intermediate Similarity	NPC188667
0.7113	Intermediate Similarity	NPC477684
0.7111	Intermediate Similarity	NPC207772
0.7111	Intermediate Similarity	NPC476808
0.7103	Intermediate Similarity	NPC5284
0.7103	Intermediate Similarity	NPC99760
0.71	Intermediate Similarity	NPC91439
0.7097	Intermediate Similarity	NPC110150
0.7097	Intermediate Similarity	NPC66764
0.7091	Intermediate Similarity	NPC54739
0.7087	Intermediate Similarity	NPC474747
0.7087	Intermediate Similarity	NPC53222
0.7083	Intermediate Similarity	NPC476704
0.7071	Intermediate Similarity	NPC258674
0.7064	Intermediate Similarity	NPC7921
0.7064	Intermediate Similarity	NPC326264
0.7064	Intermediate Similarity	NPC49451
0.7064	Intermediate Similarity	NPC198539
0.7064	Intermediate Similarity	NPC208998
0.7053	Intermediate Similarity	NPC262026
0.7048	Intermediate Similarity	NPC470587
0.7043	Intermediate Similarity	NPC470922
0.7041	Intermediate Similarity	NPC476705
0.7041	Intermediate Similarity	NPC73457
0.7037	Intermediate Similarity	NPC317107
0.7037	Intermediate Similarity	NPC171888
0.7037	Intermediate Similarity	NPC476023
0.7037	Intermediate Similarity	NPC474229
0.7037	Intermediate Similarity	NPC201992
0.7037	Intermediate Similarity	NPC146945
0.7033	Intermediate Similarity	NPC276647
0.7033	Intermediate Similarity	NPC622
0.703	Intermediate Similarity	NPC471916
0.703	Intermediate Similarity	NPC236176
0.703	Intermediate Similarity	NPC239895
0.7027	Intermediate Similarity	NPC477116
0.7027	Intermediate Similarity	NPC27999
0.7019	Intermediate Similarity	NPC472750
0.7019	Intermediate Similarity	NPC320154
0.7019	Intermediate Similarity	NPC70967
0.7019	Intermediate Similarity	NPC33973
0.7019	Intermediate Similarity	NPC472747
0.7019	Intermediate Similarity	NPC320294
0.7019	Intermediate Similarity	NPC475871
0.7019	Intermediate Similarity	NPC475945
0.7011	Intermediate Similarity	NPC144627
0.7009	Intermediate Similarity	NPC474242
0.7009	Intermediate Similarity	NPC470257
0.7009	Intermediate Similarity	NPC141350
0.7009	Intermediate Similarity	NPC471400
0.7	Intermediate Similarity	NPC475900
0.7	Intermediate Similarity	NPC227494
0.7	Intermediate Similarity	NPC248574
0.7	Intermediate Similarity	NPC473170
0.7	Intermediate Similarity	NPC31021
0.6991	Remote Similarity	NPC112038
0.699	Remote Similarity	NPC133907
0.699	Remote Similarity	NPC185141
0.699	Remote Similarity	NPC47880
0.699	Remote Similarity	NPC46998
0.699	Remote Similarity	NPC110443
0.699	Remote Similarity	NPC128733
0.6979	Remote Similarity	NPC179659
0.6977	Remote Similarity	NPC469914
0.6972	Remote Similarity	NPC11252
0.6972	Remote Similarity	NPC472002
0.6972	Remote Similarity	NPC317687
0.6972	Remote Similarity	NPC289312
0.6972	Remote Similarity	NPC90769
0.697	Remote Similarity	NPC477615
0.6957	Remote Similarity	NPC105926
0.6957	Remote Similarity	NPC74445
0.6957	Remote Similarity	NPC91693
0.6957	Remote Similarity	NPC67251
0.6957	Remote Similarity	NPC120724
0.6957	Remote Similarity	NPC265557
0.6957	Remote Similarity	NPC18945
0.6957	Remote Similarity	NPC287817
0.6952	Remote Similarity	NPC135854
0.6952	Remote Similarity	NPC474741
0.6952	Remote Similarity	NPC2436

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 NPC269677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2444
0.2-0.3	4051
0.3-0.4	1627
0.4-0.5	507
0.5-0.6	234
0.6-0.7	75
0.7-0.8	3
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
0.7556	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7341	Phase 2
0.6991	Remote Similarity	NPD6054	Approved
0.6991	Remote Similarity	NPD6059	Approved
0.69	Remote Similarity	NPD5282	Discontinued
0.687	Remote Similarity	NPD6370	Approved
0.6842	Remote Similarity	NPD6319	Approved
0.6824	Remote Similarity	NPD7331	Phase 2
0.6789	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD6016	Approved
0.6783	Remote Similarity	NPD6015	Approved
0.6752	Remote Similarity	NPD7492	Approved
0.6739	Remote Similarity	NPD3617	Approved
0.6729	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD7128	Approved
0.6729	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6675	Approved
0.6724	Remote Similarity	NPD5988	Approved
0.6701	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6372	Approved
0.6697	Remote Similarity	NPD6373	Approved
0.6695	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD7078	Approved
0.6607	Remote Similarity	NPD4632	Approved
0.6606	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD6899	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6602	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD5329	Approved
0.6596	Remote Similarity	NPD4695	Discontinued
0.6583	Remote Similarity	NPD6033	Approved
0.6583	Remote Similarity	NPD7736	Approved
0.6579	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6650	Approved
0.6577	Remote Similarity	NPD6649	Approved
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD4755	Approved
0.6538	Remote Similarity	NPD6083	Phase 2
0.6525	Remote Similarity	NPD8328	Phase 3
0.6514	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5697	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.6505	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD6904	Approved
0.65	Remote Similarity	NPD5328	Approved
0.6495	Remote Similarity	NPD4197	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6442	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5221	Approved
0.6442	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD3704	Approved
0.6435	Remote Similarity	NPD6009	Approved
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD4700	Approved
0.6415	Remote Similarity	NPD5286	Approved
0.6415	Remote Similarity	NPD5285	Approved
0.6415	Remote Similarity	NPD4696	Approved
0.64	Remote Similarity	NPD5737	Approved
0.64	Remote Similarity	NPD6672	Approved
0.6396	Remote Similarity	NPD6014	Approved
0.6396	Remote Similarity	NPD6012	Approved
0.6396	Remote Similarity	NPD6013	Approved
0.6392	Remote Similarity	NPD6110	Phase 1
0.6387	Remote Similarity	NPD7604	Phase 2
0.6381	Remote Similarity	NPD5173	Approved
0.6373	Remote Similarity	NPD6079	Approved
0.6373	Remote Similarity	NPD6050	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD5280	Approved
0.6364	Remote Similarity	NPD5690	Phase 2
0.6364	Remote Similarity	NPD4694	Approved
0.6356	Remote Similarity	NPD5983	Phase 2
0.6355	Remote Similarity	NPD5223	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD4753	Phase 2
0.6337	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5696	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6306	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3573	Approved
0.6296	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD5224	Approved
0.6296	Remote Similarity	NPD5225	Approved
0.6296	Remote Similarity	NPD5226	Approved
0.6296	Remote Similarity	NPD4633	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD4223	Phase 3
0.6289	Remote Similarity	NPD4221	Approved
0.6281	Remote Similarity	NPD6336	Discontinued
0.6279	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5692	Phase 3
0.6273	Remote Similarity	NPD6008	Approved
0.6263	Remote Similarity	NPD1696	Phase 3
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7748	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD4754	Approved
0.6226	Remote Similarity	NPD7902	Approved
0.6216	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD5694	Approved
0.6214	Remote Similarity	NPD5693	Phase 1
0.6214	Remote Similarity	NPD6411	Approved
0.6214	Remote Similarity	NPD7983	Approved
0.62	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD6098	Approved
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD4225	Approved
0.6167	Remote Similarity	NPD8080	Discontinued
0.6162	Remote Similarity	NPD4786	Approved
0.6126	Remote Similarity	NPD4768	Approved
0.6126	Remote Similarity	NPD4767	Approved
0.6122	Remote Similarity	NPD3667	Approved
0.6117	Remote Similarity	NPD6698	Approved
0.6117	Remote Similarity	NPD46	Approved
0.6106	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6335	Approved
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD8513	Phase 3
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8517	Approved
0.6068	Remote Similarity	NPD6274	Approved
0.6068	Remote Similarity	NPD6868	Approved
0.6058	Remote Similarity	NPD7515	Phase 2
0.6053	Remote Similarity	NPD6371	Approved
0.605	Remote Similarity	NPD7101	Approved
0.605	Remote Similarity	NPD7100	Approved
0.604	Remote Similarity	NPD5205	Approved
0.604	Remote Similarity	NPD5786	Approved
0.604	Remote Similarity	NPD4138	Approved
0.604	Remote Similarity	NPD4689	Approved
0.604	Remote Similarity	NPD4693	Phase 3
0.604	Remote Similarity	NPD4688	Approved
0.604	Remote Similarity	NPD4519	Discontinued
0.604	Remote Similarity	NPD4690	Approved
0.604	Remote Similarity	NPD4623	Approved
0.604	Remote Similarity	NPD5279	Phase 3
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5210	Approved
0.6038	Remote Similarity	NPD4629	Approved
0.6038	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5654	Approved
0.602	Remote Similarity	NPD5369	Approved
0.602	Remote Similarity	NPD4692	Approved
0.602	Remote Similarity	NPD4139	Approved
0.6018	Remote Similarity	NPD5128	Approved
0.6018	Remote Similarity	NPD4729	Approved
0.6018	Remote Similarity	NPD4730	Approved
0.6017	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD5133	Approved
0.5966	Remote Similarity	NPD6313	Approved
0.5966	Remote Similarity	NPD6314	Approved
0.595	Remote Similarity	NPD6909	Approved
0.595	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6908	Approved
0.5948	Remote Similarity	NPD6053	Discontinued
0.5943	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5959	Approved
0.5918	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5135	Approved
0.5913	Remote Similarity	NPD5250	Approved
0.5913	Remote Similarity	NPD5247	Approved
0.5913	Remote Similarity	NPD5251	Approved
0.5913	Remote Similarity	NPD5249	Phase 3
0.5913	Remote Similarity	NPD5169	Approved
0.5913	Remote Similarity	NPD5248	Approved
0.5913	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5284	Approved
0.5905	Remote Similarity	NPD5281	Approved
0.5889	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5877	Remote Similarity	NPD5168	Approved
0.5873	Remote Similarity	NPD7319	Approved
0.5872	Remote Similarity	NPD7638	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