NPASS Compound

Structure

CID103743 OpenBabel06191715452D 30 31 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 26 1 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 27 2 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 29 2 0 0 0 0 24 26 1 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	457.845
LogP:	5.939
LogD:	4.746
LogS:	-4.918
# Rotatable Bonds:	7
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	4.59
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	2.273296377097722e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.461

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	93.68319702148438%
Volume Distribution (VD):	2.234
Pgp-substrate:	4.763365745544434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.691
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.19
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	12.101
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.604
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.063
Carcinogencity:	0.662
Eye Corrosion:	0.056
Eye Irritation:	0.063
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC103743

Natural Product ID:	NPC103743
*Common Name:**	Lupulone A
IUPAC Name:	7-hydroxy-2,2-dimethyl-6-(3-methylbutanoyl)-4a,8-bis(3-methylbut-2-enyl)chromen-5-one
Synonyms:
Standard InCHIKey:	WOAGFYGUGHOSMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H36O4/c1-16(2)9-10-19-22(28)21(20(27)15-18(5)6)23(29)26(12-11-17(3)4)14-13-25(7,8)30-24(19)26/h9,11,13-14,18,28H,10,12,15H2,1-8H3
SMILES:	CC(=CCC1=C2C(CC=C(C)C)(C=CC(C)(C)O2)C(=O)C(=C1O)C(=O)CC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480268
PubChem CID:	11223675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans

*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
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13879	Humulus lupulus	Species	Cannabaceae	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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20000.0	nM	PMID[506986]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	40.0	%	PMID[506986]

☑ 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 NPC103743 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	194
0.1-0.2	1164
0.2-0.3	4542
0.3-0.4	9981
0.4-0.5	16775
0.5-0.6	7483
0.6-0.7	2324
0.7-0.8	211
0.8-0.85	10
0.85-0.9	7
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC113370
1.0	High Similarity	NPC476079
0.9753	High Similarity	NPC307112
0.9506	High Similarity	NPC475083
0.8539	High Similarity	NPC280592
0.8539	High Similarity	NPC213636
0.8539	High Similarity	NPC253177
0.8444	Intermediate Similarity	NPC296114
0.8444	Intermediate Similarity	NPC471329
0.8261	Intermediate Similarity	NPC477241
0.8222	Intermediate Similarity	NPC472688
0.8222	Intermediate Similarity	NPC472676
0.8214	Intermediate Similarity	NPC315765
0.8191	Intermediate Similarity	NPC239895
0.814	Intermediate Similarity	NPC275766
0.7938	Intermediate Similarity	NPC469851
0.7912	Intermediate Similarity	NPC143025
0.7912	Intermediate Similarity	NPC58532
0.7912	Intermediate Similarity	NPC472677
0.7895	Intermediate Similarity	NPC135576
0.7895	Intermediate Similarity	NPC93271
0.7882	Intermediate Similarity	NPC316324
0.7849	Intermediate Similarity	NPC45579
0.7805	Intermediate Similarity	NPC203819
0.7766	Intermediate Similarity	NPC248193
0.7753	Intermediate Similarity	NPC288281
0.7753	Intermediate Similarity	NPC16488
0.7717	Intermediate Similarity	NPC60765
0.7692	Intermediate Similarity	NPC316426
0.7692	Intermediate Similarity	NPC315395
0.766	Intermediate Similarity	NPC166110
0.7624	Intermediate Similarity	NPC469852
0.7586	Intermediate Similarity	NPC248624
0.7528	Intermediate Similarity	NPC44963
0.7528	Intermediate Similarity	NPC189237
0.7528	Intermediate Similarity	NPC472684
0.7527	Intermediate Similarity	NPC26078
0.7527	Intermediate Similarity	NPC473658
0.75	Intermediate Similarity	NPC234038
0.75	Intermediate Similarity	NPC477479
0.75	Intermediate Similarity	NPC477478
0.7475	Intermediate Similarity	NPC54705
0.7474	Intermediate Similarity	NPC193396
0.7474	Intermediate Similarity	NPC32944
0.7474	Intermediate Similarity	NPC472705
0.7474	Intermediate Similarity	NPC32552
0.7449	Intermediate Similarity	NPC208094
0.7449	Intermediate Similarity	NPC478233
0.7449	Intermediate Similarity	NPC53844
0.7447	Intermediate Similarity	NPC284561
0.7447	Intermediate Similarity	NPC51358
0.7447	Intermediate Similarity	NPC142159
0.7447	Intermediate Similarity	NPC95364
0.7447	Intermediate Similarity	NPC36668
0.7447	Intermediate Similarity	NPC118011
0.7447	Intermediate Similarity	NPC307092
0.7423	Intermediate Similarity	NPC209355
0.7423	Intermediate Similarity	NPC295347
0.7419	Intermediate Similarity	NPC125925
0.7404	Intermediate Similarity	NPC137911
0.7404	Intermediate Similarity	NPC228477
0.74	Intermediate Similarity	NPC244456
0.74	Intermediate Similarity	NPC469657
0.74	Intermediate Similarity	NPC206079
0.7396	Intermediate Similarity	NPC282644
0.7396	Intermediate Similarity	NPC29798
0.7391	Intermediate Similarity	NPC470177
0.7386	Intermediate Similarity	NPC275494
0.7386	Intermediate Similarity	NPC471409
0.7386	Intermediate Similarity	NPC478246
0.7386	Intermediate Similarity	NPC478247
0.7381	Intermediate Similarity	NPC316029
0.7381	Intermediate Similarity	NPC315597
0.7374	Intermediate Similarity	NPC64742
0.7374	Intermediate Similarity	NPC35717
0.7368	Intermediate Similarity	NPC145666
0.7363	Intermediate Similarity	NPC258985
0.7347	Intermediate Similarity	NPC472733
0.7347	Intermediate Similarity	NPC472734
0.7347	Intermediate Similarity	NPC9812
0.734	Intermediate Similarity	NPC478261
0.734	Intermediate Similarity	NPC72397
0.734	Intermediate Similarity	NPC478259
0.734	Intermediate Similarity	NPC53454
0.734	Intermediate Similarity	NPC478260
0.732	Intermediate Similarity	NPC65829
0.7312	Intermediate Similarity	NPC198314
0.7308	Intermediate Similarity	NPC220155
0.7292	Intermediate Similarity	NPC478243
0.7292	Intermediate Similarity	NPC478244
0.7283	Intermediate Similarity	NPC196487
0.7283	Intermediate Similarity	NPC14575
0.7282	Intermediate Similarity	NPC478052
0.7282	Intermediate Similarity	NPC85529
0.7282	Intermediate Similarity	NPC32006
0.7273	Intermediate Similarity	NPC202705
0.7273	Intermediate Similarity	NPC472731
0.7273	Intermediate Similarity	NPC472732
0.7273	Intermediate Similarity	NPC315394
0.7263	Intermediate Similarity	NPC471054
0.7263	Intermediate Similarity	NPC474918
0.7263	Intermediate Similarity	NPC212598
0.7262	Intermediate Similarity	NPC473277
0.7255	Intermediate Similarity	NPC25666
0.7255	Intermediate Similarity	NPC297281
0.7255	Intermediate Similarity	NPC473144
0.7255	Intermediate Similarity	NPC271059
0.7253	Intermediate Similarity	NPC85772
0.7245	Intermediate Similarity	NPC171395
0.7234	Intermediate Similarity	NPC23622
0.7234	Intermediate Similarity	NPC478145
0.7229	Intermediate Similarity	NPC278895
0.7228	Intermediate Similarity	NPC224172
0.7222	Intermediate Similarity	NPC160582
0.7212	Intermediate Similarity	NPC469853
0.7204	Intermediate Similarity	NPC15807
0.7204	Intermediate Similarity	NPC11804
0.7204	Intermediate Similarity	NPC281172
0.7204	Intermediate Similarity	NPC261380
0.72	Intermediate Similarity	NPC472730
0.72	Intermediate Similarity	NPC316598
0.72	Intermediate Similarity	NPC153776
0.72	Intermediate Similarity	NPC306908
0.72	Intermediate Similarity	NPC472729
0.72	Intermediate Similarity	NPC177680
0.72	Intermediate Similarity	NPC244411
0.7191	Intermediate Similarity	NPC478122
0.7188	Intermediate Similarity	NPC265856
0.7188	Intermediate Similarity	NPC476437
0.7188	Intermediate Similarity	NPC212369
0.7188	Intermediate Similarity	NPC469464
0.7188	Intermediate Similarity	NPC476369
0.7188	Intermediate Similarity	NPC113393
0.7176	Intermediate Similarity	NPC315285
0.7174	Intermediate Similarity	NPC161045
0.7172	Intermediate Similarity	NPC472675
0.7172	Intermediate Similarity	NPC21681
0.7159	Intermediate Similarity	NPC271070
0.7158	Intermediate Similarity	NPC106051
0.7158	Intermediate Similarity	NPC472008
0.7143	Intermediate Similarity	NPC473807
0.7143	Intermediate Similarity	NPC313444
0.7143	Intermediate Similarity	NPC469819
0.7143	Intermediate Similarity	NPC476415
0.7143	Intermediate Similarity	NPC478262
0.7143	Intermediate Similarity	NPC470298
0.7143	Intermediate Similarity	NPC114162
0.7143	Intermediate Similarity	NPC225515
0.7143	Intermediate Similarity	NPC53685
0.713	Intermediate Similarity	NPC321496
0.7129	Intermediate Similarity	NPC472727
0.7129	Intermediate Similarity	NPC472728
0.7128	Intermediate Similarity	NPC116575
0.7128	Intermediate Similarity	NPC291712
0.7128	Intermediate Similarity	NPC476982
0.7128	Intermediate Similarity	NPC203795
0.7128	Intermediate Similarity	NPC472009
0.7128	Intermediate Similarity	NPC470345
0.7128	Intermediate Similarity	NPC220478
0.7126	Intermediate Similarity	NPC122244
0.7111	Intermediate Similarity	NPC469617
0.7103	Intermediate Similarity	NPC474315
0.7103	Intermediate Similarity	NPC324683
0.71	Intermediate Similarity	NPC27105
0.71	Intermediate Similarity	NPC134083
0.7097	Intermediate Similarity	NPC476412
0.7097	Intermediate Similarity	NPC31086
0.7093	Intermediate Similarity	NPC84790
0.7087	Intermediate Similarity	NPC475526
0.7087	Intermediate Similarity	NPC473283
0.7087	Intermediate Similarity	NPC473624
0.7087	Intermediate Similarity	NPC329345
0.7083	Intermediate Similarity	NPC115179
0.7083	Intermediate Similarity	NPC210216
0.7083	Intermediate Similarity	NPC280833
0.7083	Intermediate Similarity	NPC106040
0.7071	Intermediate Similarity	NPC91408
0.7065	Intermediate Similarity	NPC227925
0.7059	Intermediate Similarity	NPC469914
0.7059	Intermediate Similarity	NPC62670
0.7059	Intermediate Similarity	NPC472637
0.7059	Intermediate Similarity	NPC116139
0.7053	Intermediate Similarity	NPC478144
0.7053	Intermediate Similarity	NPC181327
0.7053	Intermediate Similarity	NPC86005
0.7053	Intermediate Similarity	NPC171722
0.7053	Intermediate Similarity	NPC476409
0.7053	Intermediate Similarity	NPC38885
0.7053	Intermediate Similarity	NPC241054
0.7053	Intermediate Similarity	NPC472007
0.7053	Intermediate Similarity	NPC287079
0.7048	Intermediate Similarity	NPC199107
0.7048	Intermediate Similarity	NPC91034
0.7048	Intermediate Similarity	NPC232969
0.7041	Intermediate Similarity	NPC476416
0.7041	Intermediate Similarity	NPC476049
0.703	Intermediate Similarity	NPC203388
0.703	Intermediate Similarity	NPC166770
0.703	Intermediate Similarity	NPC471331
0.703	Intermediate Similarity	NPC471330

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 NPC103743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1468
0.2-0.3	3543
0.3-0.4	2636
0.4-0.5	945
0.5-0.6	317
0.6-0.7	49
0.7-0.8	1
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
0.7108	Intermediate Similarity	NPD7331	Phase 2
0.7041	Intermediate Similarity	NPD5779	Approved
0.7041	Intermediate Similarity	NPD5778	Approved
0.701	Intermediate Similarity	NPD5785	Approved
0.6939	Remote Similarity	NPD6411	Approved
0.6889	Remote Similarity	NPD4756	Discovery
0.6854	Remote Similarity	NPD8039	Approved
0.6848	Remote Similarity	NPD4695	Discontinued
0.6848	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5282	Discontinued
0.6786	Remote Similarity	NPD7341	Phase 2
0.6771	Remote Similarity	NPD4623	Approved
0.6771	Remote Similarity	NPD4519	Discontinued
0.6735	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6101	Approved
0.6702	Remote Similarity	NPD5209	Approved
0.6637	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD4518	Approved
0.6632	Remote Similarity	NPD7154	Phase 3
0.66	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD7983	Approved
0.6569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7839	Suspended
0.6495	Remote Similarity	NPD1696	Phase 3
0.6495	Remote Similarity	NPD5363	Approved
0.6436	Remote Similarity	NPD5284	Approved
0.6436	Remote Similarity	NPD5281	Approved
0.6429	Remote Similarity	NPD4694	Approved
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD5280	Approved
0.6381	Remote Similarity	NPD4225	Approved
0.6354	Remote Similarity	NPD4223	Phase 3
0.6354	Remote Similarity	NPD4221	Approved
0.6354	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4269	Approved
0.6354	Remote Similarity	NPD4270	Approved
0.6353	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6698	Approved
0.6337	Remote Similarity	NPD46	Approved
0.6327	Remote Similarity	NPD1694	Approved
0.6327	Remote Similarity	NPD5329	Approved
0.6322	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8264	Approved
0.6289	Remote Similarity	NPD6110	Phase 1
0.6283	Remote Similarity	NPD6053	Discontinued
0.6277	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5693	Phase 1
0.6275	Remote Similarity	NPD6050	Approved
0.6275	Remote Similarity	NPD5694	Approved
0.6263	Remote Similarity	NPD5279	Phase 3
0.6263	Remote Similarity	NPD5690	Phase 2
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD5909	Discontinued
0.6235	Remote Similarity	NPD4193	Approved
0.6235	Remote Similarity	NPD4192	Approved
0.6235	Remote Similarity	NPD4194	Approved
0.6235	Remote Similarity	NPD4191	Approved
0.6224	Remote Similarity	NPD4197	Approved
0.62	Remote Similarity	NPD3573	Approved
0.6176	Remote Similarity	NPD5692	Phase 3
0.6176	Remote Similarity	NPD5207	Approved
0.6176	Remote Similarity	NPD4096	Approved
0.6176	Remote Similarity	NPD7838	Discovery
0.6168	Remote Similarity	NPD7639	Approved
0.6168	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7748	Approved
0.6146	Remote Similarity	NPD4252	Approved
0.6136	Remote Similarity	NPD3704	Approved
0.6134	Remote Similarity	NPD8513	Phase 3
0.6132	Remote Similarity	NPD6084	Phase 2
0.6132	Remote Similarity	NPD6083	Phase 2
0.6122	Remote Similarity	NPD5362	Discontinued
0.6122	Remote Similarity	NPD6695	Phase 3
0.6117	Remote Similarity	NPD6079	Approved
0.6105	Remote Similarity	NPD3617	Approved
0.6105	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4689	Approved
0.61	Remote Similarity	NPD4138	Approved
0.61	Remote Similarity	NPD5205	Approved
0.61	Remote Similarity	NPD4688	Approved
0.61	Remote Similarity	NPD4690	Approved
0.61	Remote Similarity	NPD4693	Phase 3
0.6095	Remote Similarity	NPD5695	Phase 3
0.6092	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4753	Phase 2
0.6078	Remote Similarity	NPD6080	Approved
0.6078	Remote Similarity	NPD5328	Approved
0.6078	Remote Similarity	NPD6904	Approved
0.6078	Remote Similarity	NPD6673	Approved
0.6075	Remote Similarity	NPD7638	Approved
0.6068	Remote Similarity	NPD7500	Approved
0.6061	Remote Similarity	NPD3133	Approved
0.6061	Remote Similarity	NPD4786	Approved
0.6061	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3665	Phase 1
0.6061	Remote Similarity	NPD3666	Approved
0.6058	Remote Similarity	NPD6399	Phase 3
0.6055	Remote Similarity	NPD5211	Phase 2
0.6053	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4195	Approved
0.6022	Remote Similarity	NPD4687	Approved
0.6022	Remote Similarity	NPD4058	Approved
0.6022	Remote Similarity	NPD5733	Approved
0.602	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	Approved
0.5981	Remote Similarity	NPD7902	Approved
0.598	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD6672	Approved
0.5979	Remote Similarity	NPD7332	Phase 2
0.5979	Remote Similarity	NPD7514	Phase 3
0.5979	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4821	Approved
0.5979	Remote Similarity	NPD4820	Approved
0.5979	Remote Similarity	NPD4822	Approved
0.5979	Remote Similarity	NPD4819	Approved
0.5978	Remote Similarity	NPD5276	Approved
0.5962	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7515	Phase 2
0.5946	Remote Similarity	NPD5141	Approved
0.5943	Remote Similarity	NPD5210	Approved
0.5943	Remote Similarity	NPD4629	Approved
0.5941	Remote Similarity	NPD3618	Phase 1
0.5941	Remote Similarity	NPD7334	Approved
0.5941	Remote Similarity	NPD5330	Approved
0.5941	Remote Similarity	NPD6684	Approved
0.5941	Remote Similarity	NPD7521	Approved
0.5941	Remote Similarity	NPD7146	Approved
0.5941	Remote Similarity	NPD6409	Approved
0.5929	Remote Similarity	NPD6881	Approved
0.5929	Remote Similarity	NPD6899	Approved
0.5926	Remote Similarity	NPD5696	Approved
0.5922	Remote Similarity	NPD5370	Suspended
0.5905	Remote Similarity	NPD5133	Approved
0.5893	Remote Similarity	NPD7128	Approved
0.5893	Remote Similarity	NPD6675	Approved
0.5893	Remote Similarity	NPD5739	Approved
0.5893	Remote Similarity	NPD6402	Approved
0.5888	Remote Similarity	NPD5222	Approved
0.5888	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5221	Approved
0.5882	Remote Similarity	NPD7750	Discontinued
0.5882	Remote Similarity	NPD4251	Approved
0.5882	Remote Similarity	NPD7524	Approved
0.5882	Remote Similarity	NPD4250	Approved
0.5872	Remote Similarity	NPD6648	Approved
0.5872	Remote Similarity	NPD4696	Approved
0.5872	Remote Similarity	NPD5285	Approved
0.5872	Remote Similarity	NPD5286	Approved
0.5872	Remote Similarity	NPD6404	Discontinued
0.5859	Remote Similarity	NPD6435	Approved
0.5851	Remote Similarity	NPD6926	Approved
0.5851	Remote Similarity	NPD6924	Approved
0.5849	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5697	Approved
0.5841	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD5173	Approved
0.5827	Remote Similarity	NPD7260	Phase 2
0.5826	Remote Similarity	NPD7102	Approved
0.5826	Remote Similarity	NPD6883	Approved
0.5826	Remote Similarity	NPD7290	Approved
0.5825	Remote Similarity	NPD5208	Approved
0.5825	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6903	Approved
0.5818	Remote Similarity	NPD5223	Approved
0.5816	Remote Similarity	NPD6931	Approved
0.5816	Remote Similarity	NPD6930	Phase 2
0.58	Remote Similarity	NPD5332	Approved
0.58	Remote Similarity	NPD5331	Approved
0.5794	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5654	Approved
0.5789	Remote Similarity	NPD7320	Approved
0.5789	Remote Similarity	NPD6686	Approved
0.5789	Remote Similarity	NPD6011	Approved
0.5785	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6098	Approved
0.5784	Remote Similarity	NPD4249	Approved
0.5776	Remote Similarity	NPD6847	Approved
0.5776	Remote Similarity	NPD6869	Approved
0.5776	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6650	Approved
0.5776	Remote Similarity	NPD6617	Approved
0.5776	Remote Similarity	NPD6649	Approved
0.5776	Remote Similarity	NPD8130	Phase 1
0.5773	Remote Similarity	NPD4268	Approved
0.5773	Remote Similarity	NPD7145	Approved
0.5773	Remote Similarity	NPD4271	Approved
0.5766	Remote Similarity	NPD5225	Approved
0.5766	Remote Similarity	NPD4633	Approved
0.5766	Remote Similarity	NPD5226	Approved
0.5766	Remote Similarity	NPD5224	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