NPASS Compound

Structure

CID93271 OpenBabel06191715432D 31 32 0 0 1 0 0 0 0 0999 V2000 1.8171 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1713 4.0497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5890 4.7541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 3.0316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1767 3.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 17 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 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 14 26 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 20 25 1 0 0 0 0 20 31 1 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 31 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.27
Volume:	469.272
LogP:	4.919
LogD:	3.536
LogS:	-4.477
# Rotatable Bonds:	8
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	4.724
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.706
MDCK Permeability:	2.176193447667174e-05
Pgp-inhibitor:	0.308
Pgp-substrate:	0.59
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.872
30% Bioavailability (F30%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	93.32594299316406%
Volume Distribution (VD):	2.036
Pgp-substrate:	5.956106185913086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.416
CYP2C9-substrate:	0.603
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.672
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	9.295
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.568
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.066
Carcinogencity:	0.307
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC93271

Natural Product ID:	NPC93271
*Common Name:**	Lupulone D
IUPAC Name:	6-hydroxy-2-(2-hydroxypropan-2-yl)-5-(3-methylbutanoyl)-3a,7-bis(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-4-one
Synonyms:	Lupulone D
Standard InCHIKey:	UFNSPVPZCKZBHN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H38O5/c1-15(2)9-10-18-22(28)21(19(27)13-17(5)6)23(29)26(12-11-16(3)4)14-20(25(7,8)30)31-24(18)26/h9,11,17,20,28,30H,10,12-14H2,1-8H3
SMILES:	CC(=CCC1=C2C(CC=C(C)C)(CC(C(C)(C)O)O2)C(=O)C(=C1O)C(=O)CC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521269
PubChem CID:	11350917
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11000.0	nM	PMID[460831]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	<	80.0	%	PMID[460831]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	40.0	%	PMID[460831]

☑ 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 NPC93271 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	187
0.1-0.2	1051
0.2-0.3	4179
0.3-0.4	8233
0.4-0.5	15416
0.5-0.6	8579
0.6-0.7	4473
0.7-0.8	546
0.8-0.85	15
0.85-0.9	13
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135576
0.913	High Similarity	NPC114162
0.913	High Similarity	NPC469819
0.9043	High Similarity	NPC239895
0.8925	High Similarity	NPC477241
0.8842	High Similarity	NPC27105
0.875	High Similarity	NPC471331
0.875	High Similarity	NPC99657
0.875	High Similarity	NPC472687
0.875	High Similarity	NPC203388
0.875	High Similarity	NPC471330
0.8387	Intermediate Similarity	NPC87189
0.8387	Intermediate Similarity	NPC228415
0.8351	Intermediate Similarity	NPC472733
0.8351	Intermediate Similarity	NPC472734
0.8265	Intermediate Similarity	NPC472732
0.8265	Intermediate Similarity	NPC472731
0.8235	Intermediate Similarity	NPC471333
0.8235	Intermediate Similarity	NPC471332
0.8182	Intermediate Similarity	NPC472729
0.8182	Intermediate Similarity	NPC153776
0.8182	Intermediate Similarity	NPC472730
0.8182	Intermediate Similarity	NPC177680
0.8125	Intermediate Similarity	NPC476705
0.8111	Intermediate Similarity	NPC472948
0.81	Intermediate Similarity	NPC472727
0.81	Intermediate Similarity	NPC472728
0.8085	Intermediate Similarity	NPC23622
0.802	Intermediate Similarity	NPC471401
0.802	Intermediate Similarity	NPC9878
0.8	Intermediate Similarity	NPC472677
0.8	Intermediate Similarity	NPC58532
0.7941	Intermediate Similarity	NPC70369
0.7895	Intermediate Similarity	NPC113370
0.7895	Intermediate Similarity	NPC476079
0.7895	Intermediate Similarity	NPC103743
0.7864	Intermediate Similarity	NPC472755
0.7857	Intermediate Similarity	NPC61275
0.7843	Intermediate Similarity	NPC472753
0.7835	Intermediate Similarity	NPC166554
0.7826	Intermediate Similarity	NPC275766
0.7812	Intermediate Similarity	NPC476708
0.7812	Intermediate Similarity	NPC476707
0.7812	Intermediate Similarity	NPC472008
0.7812	Intermediate Similarity	NPC476706
0.78	Intermediate Similarity	NPC21681
0.78	Intermediate Similarity	NPC472675
0.7767	Intermediate Similarity	NPC472754
0.7755	Intermediate Similarity	NPC146852
0.7708	Intermediate Similarity	NPC472007
0.7708	Intermediate Similarity	NPC38885
0.7708	Intermediate Similarity	NPC179659
0.7684	Intermediate Similarity	NPC307112
0.767	Intermediate Similarity	NPC181645
0.7664	Intermediate Similarity	NPC38154
0.7653	Intermediate Similarity	NPC51004
0.7653	Intermediate Similarity	NPC474761
0.7653	Intermediate Similarity	NPC476004
0.7653	Intermediate Similarity	NPC265856
0.7647	Intermediate Similarity	NPC35717
0.7647	Intermediate Similarity	NPC300584
0.7647	Intermediate Similarity	NPC278008
0.7629	Intermediate Similarity	NPC143025
0.7619	Intermediate Similarity	NPC472756
0.7611	Intermediate Similarity	NPC478051
0.7604	Intermediate Similarity	NPC472009
0.7576	Intermediate Similarity	NPC30515
0.7576	Intermediate Similarity	NPC475441
0.7573	Intermediate Similarity	NPC54705
0.7551	Intermediate Similarity	NPC307411
0.7551	Intermediate Similarity	NPC295448
0.7549	Intermediate Similarity	NPC134454
0.7549	Intermediate Similarity	NPC17326
0.7549	Intermediate Similarity	NPC20066
0.7549	Intermediate Similarity	NPC40812
0.7547	Intermediate Similarity	NPC472749
0.7547	Intermediate Similarity	NPC472751
0.7545	Intermediate Similarity	NPC469454
0.7545	Intermediate Similarity	NPC469463
0.7545	Intermediate Similarity	NPC469496
0.7525	Intermediate Similarity	NPC36954
0.7524	Intermediate Similarity	NPC472747
0.7524	Intermediate Similarity	NPC472750
0.7524	Intermediate Similarity	NPC110989
0.7524	Intermediate Similarity	NPC475321
0.7523	Intermediate Similarity	NPC304180
0.7523	Intermediate Similarity	NPC179798
0.7523	Intermediate Similarity	NPC188738
0.7523	Intermediate Similarity	NPC324683
0.75	Intermediate Similarity	NPC474742
0.75	Intermediate Similarity	NPC471400
0.75	Intermediate Similarity	NPC475912
0.75	Intermediate Similarity	NPC476300
0.7477	Intermediate Similarity	NPC247069
0.7476	Intermediate Similarity	NPC187761
0.7476	Intermediate Similarity	NPC177232
0.7476	Intermediate Similarity	NPC83895
0.7476	Intermediate Similarity	NPC212465
0.7475	Intermediate Similarity	NPC51653
0.7475	Intermediate Similarity	NPC469464
0.7475	Intermediate Similarity	NPC313670
0.7474	Intermediate Similarity	NPC475083
0.7455	Intermediate Similarity	NPC269530
0.7455	Intermediate Similarity	NPC66108
0.7455	Intermediate Similarity	NPC207251
0.7453	Intermediate Similarity	NPC475676
0.7453	Intermediate Similarity	NPC220964
0.7453	Intermediate Similarity	NPC203659
0.7453	Intermediate Similarity	NPC146731
0.7453	Intermediate Similarity	NPC100487
0.7453	Intermediate Similarity	NPC472748
0.7451	Intermediate Similarity	NPC11396
0.7451	Intermediate Similarity	NPC8803
0.7451	Intermediate Similarity	NPC21302
0.7449	Intermediate Similarity	NPC476704
0.7431	Intermediate Similarity	NPC286880
0.7431	Intermediate Similarity	NPC478211
0.7429	Intermediate Similarity	NPC225353
0.7429	Intermediate Similarity	NPC183571
0.7429	Intermediate Similarity	NPC149371
0.7426	Intermediate Similarity	NPC196227
0.7426	Intermediate Similarity	NPC81386
0.7426	Intermediate Similarity	NPC14322
0.7426	Intermediate Similarity	NPC65829
0.7426	Intermediate Similarity	NPC474035
0.7423	Intermediate Similarity	NPC164393
0.7419	Intermediate Similarity	NPC258231
0.7404	Intermediate Similarity	NPC288876
0.74	Intermediate Similarity	NPC230623
0.74	Intermediate Similarity	NPC184463
0.74	Intermediate Similarity	NPC472705
0.74	Intermediate Similarity	NPC116726
0.7387	Intermediate Similarity	NPC56448
0.7383	Intermediate Similarity	NPC469852
0.7383	Intermediate Similarity	NPC32006
0.7383	Intermediate Similarity	NPC478052
0.7383	Intermediate Similarity	NPC85529
0.7379	Intermediate Similarity	NPC473574
0.7379	Intermediate Similarity	NPC161147
0.7379	Intermediate Similarity	NPC53844
0.7379	Intermediate Similarity	NPC20078
0.7374	Intermediate Similarity	NPC472676
0.7374	Intermediate Similarity	NPC472688
0.7364	Intermediate Similarity	NPC247031
0.7364	Intermediate Similarity	NPC132790
0.7364	Intermediate Similarity	NPC100329
0.7364	Intermediate Similarity	NPC97939
0.7358	Intermediate Similarity	NPC474165
0.7358	Intermediate Similarity	NPC475945
0.7358	Intermediate Similarity	NPC69171
0.7358	Intermediate Similarity	NPC475871
0.7358	Intermediate Similarity	NPC473624
0.7358	Intermediate Similarity	NPC4620
0.7353	Intermediate Similarity	NPC270013
0.7353	Intermediate Similarity	NPC214694
0.7353	Intermediate Similarity	NPC14961
0.7347	Intermediate Similarity	NPC86005
0.7345	Intermediate Similarity	NPC23046
0.7345	Intermediate Similarity	NPC471145
0.734	Intermediate Similarity	NPC470946
0.734	Intermediate Similarity	NPC470947
0.734	Intermediate Similarity	NPC470945
0.7339	Intermediate Similarity	NPC87335
0.7339	Intermediate Similarity	NPC470257
0.7333	Intermediate Similarity	NPC47880
0.7333	Intermediate Similarity	NPC46998
0.7333	Intermediate Similarity	NPC101067
0.7333	Intermediate Similarity	NPC110443
0.7333	Intermediate Similarity	NPC185141
0.7333	Intermediate Similarity	NPC476134
0.7333	Intermediate Similarity	NPC133907
0.7333	Intermediate Similarity	NPC128733
0.7327	Intermediate Similarity	NPC469692
0.7327	Intermediate Similarity	NPC469645
0.7327	Intermediate Similarity	NPC179746
0.7327	Intermediate Similarity	NPC288240
0.7327	Intermediate Similarity	NPC81419
0.7327	Intermediate Similarity	NPC162205
0.7327	Intermediate Similarity	NPC295204
0.7327	Intermediate Similarity	NPC273579
0.7321	Intermediate Similarity	NPC326542
0.732	Intermediate Similarity	NPC68303
0.732	Intermediate Similarity	NPC137033
0.732	Intermediate Similarity	NPC21469
0.732	Intermediate Similarity	NPC307126
0.732	Intermediate Similarity	NPC15807
0.7315	Intermediate Similarity	NPC473169
0.7308	Intermediate Similarity	NPC261377
0.7308	Intermediate Similarity	NPC306908
0.7308	Intermediate Similarity	NPC308567
0.7308	Intermediate Similarity	NPC255592
0.7303	Intermediate Similarity	NPC203819
0.73	Intermediate Similarity	NPC280592
0.73	Intermediate Similarity	NPC253177
0.73	Intermediate Similarity	NPC230332
0.73	Intermediate Similarity	NPC213636
0.73	Intermediate Similarity	NPC316228
0.73	Intermediate Similarity	NPC473455
0.7297	Intermediate Similarity	NPC138757
0.7292	Intermediate Similarity	NPC477785

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 NPC93271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1497
0.2-0.3	3783
0.3-0.4	2477
0.4-0.5	808
0.5-0.6	290
0.6-0.7	130
0.7-0.8	6
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
0.76	Intermediate Similarity	NPD5282	Discontinued
0.74	Intermediate Similarity	NPD7983	Approved
0.7327	Intermediate Similarity	NPD5778	Approved
0.7327	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD6110	Phase 1
0.7188	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6371	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6857	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7331	Phase 2
0.6847	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4225	Approved
0.6796	Remote Similarity	NPD5785	Approved
0.6796	Remote Similarity	NPD6698	Approved
0.6796	Remote Similarity	NPD46	Approved
0.6792	Remote Similarity	NPD7839	Suspended
0.6752	Remote Similarity	NPD7115	Discovery
0.6742	Remote Similarity	NPD7341	Phase 2
0.6733	Remote Similarity	NPD5786	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6634	Remote Similarity	NPD5363	Approved
0.66	Remote Similarity	NPD7154	Phase 3
0.6583	Remote Similarity	NPD6059	Approved
0.6583	Remote Similarity	NPD6054	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD5279	Phase 3
0.6549	Remote Similarity	NPD6412	Phase 2
0.6538	Remote Similarity	NPD5328	Approved
0.6522	Remote Similarity	NPD4634	Approved
0.6514	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4269	Approved
0.65	Remote Similarity	NPD4270	Approved
0.6495	Remote Similarity	NPD4756	Discovery
0.6491	Remote Similarity	NPD6686	Approved
0.6476	Remote Similarity	NPD7838	Discovery
0.6475	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1694	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6436	Remote Similarity	NPD6695	Phase 3
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6079	Approved
0.641	Remote Similarity	NPD6053	Discontinued
0.6408	Remote Similarity	NPD3618	Phase 1
0.6408	Remote Similarity	NPD4519	Discontinued
0.6408	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4623	Approved
0.64	Remote Similarity	NPD8074	Phase 3
0.64	Remote Similarity	NPD5369	Approved
0.6393	Remote Similarity	NPD6016	Approved
0.6393	Remote Similarity	NPD6015	Approved
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3665	Phase 1
0.6373	Remote Similarity	NPD3666	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6356	Remote Similarity	NPD4632	Approved
0.6355	Remote Similarity	NPD6399	Phase 3
0.6341	Remote Similarity	NPD5988	Approved
0.6339	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD5209	Approved
0.633	Remote Similarity	NPD4697	Phase 3
0.6328	Remote Similarity	NPD7260	Phase 2
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6616	Approved
0.6316	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6311	Remote Similarity	NPD1696	Phase 3
0.6306	Remote Similarity	NPD7639	Approved
0.6306	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD4252	Approved
0.63	Remote Similarity	NPD4695	Discontinued
0.63	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7748	Approved
0.6293	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD6373	Approved
0.629	Remote Similarity	NPD8328	Phase 3
0.6289	Remote Similarity	NPD8039	Approved
0.6273	Remote Similarity	NPD7902	Approved
0.6273	Remote Similarity	NPD6084	Phase 2
0.6273	Remote Similarity	NPD4755	Approved
0.6273	Remote Similarity	NPD6083	Phase 2
0.6271	Remote Similarity	NPD8297	Approved
0.627	Remote Similarity	NPD7078	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6262	Remote Similarity	NPD5281	Approved
0.6262	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD4694	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD5280	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD5695	Phase 3
0.6228	Remote Similarity	NPD5141	Approved
0.6226	Remote Similarity	NPD4753	Phase 2
0.622	Remote Similarity	NPD6033	Approved
0.622	Remote Similarity	NPD7736	Approved
0.6216	Remote Similarity	NPD7638	Approved
0.6216	Remote Similarity	NPD5696	Approved
0.6214	Remote Similarity	NPD4786	Approved
0.6207	Remote Similarity	NPD6881	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD6899	Approved
0.6198	Remote Similarity	NPD7500	Approved
0.619	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD7750	Discontinued
0.619	Remote Similarity	NPD4251	Approved
0.6186	Remote Similarity	NPD6649	Approved
0.6186	Remote Similarity	NPD6650	Approved
0.6182	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5222	Approved
0.6182	Remote Similarity	NPD5221	Approved
0.6176	Remote Similarity	NPD3667	Approved
0.6176	Remote Similarity	NPD6435	Approved
0.6176	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4223	Phase 3
0.6176	Remote Similarity	NPD4221	Approved
0.6172	Remote Similarity	NPD7319	Approved
0.6168	Remote Similarity	NPD5207	Approved
0.6161	Remote Similarity	NPD4700	Approved
0.6161	Remote Similarity	NPD5286	Approved
0.6161	Remote Similarity	NPD4696	Approved
0.6161	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD5329	Approved
0.6139	Remote Similarity	NPD6931	Approved
0.6139	Remote Similarity	NPD6930	Phase 2
0.6132	Remote Similarity	NPD5737	Approved
0.6132	Remote Similarity	NPD6903	Approved
0.6132	Remote Similarity	NPD4518	Approved
0.6132	Remote Similarity	NPD6672	Approved
0.6132	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5173	Approved
0.6124	Remote Similarity	NPD6914	Discontinued
0.6121	Remote Similarity	NPD5697	Approved
0.6121	Remote Similarity	NPD5701	Approved
0.6117	Remote Similarity	NPD5362	Discontinued
0.6111	Remote Similarity	NPD7515	Phase 2
0.6111	Remote Similarity	NPD8340	Approved
0.6111	Remote Similarity	NPD8299	Approved
0.6111	Remote Similarity	NPD8342	Approved
0.6111	Remote Similarity	NPD6050	Approved
0.6111	Remote Similarity	NPD8341	Approved
0.6106	Remote Similarity	NPD5223	Approved
0.6102	Remote Similarity	NPD7290	Approved
0.6102	Remote Similarity	NPD6883	Approved
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7102	Approved
0.6095	Remote Similarity	NPD4249	Approved
0.6091	Remote Similarity	NPD5210	Approved
0.6091	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4629	Approved
0.609	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6011	Approved
0.6066	Remote Similarity	NPD6009	Approved
0.6063	Remote Similarity	NPD7507	Approved
0.6061	Remote Similarity	NPD6933	Approved
0.6058	Remote Similarity	NPD4197	Approved
0.6055	Remote Similarity	NPD4202	Approved
0.6053	Remote Similarity	NPD4633	Approved
0.6053	Remote Similarity	NPD5224	Approved
0.6053	Remote Similarity	NPD5225	Approved
0.6053	Remote Similarity	NPD5226	Approved
0.605	Remote Similarity	NPD6869	Approved
0.605	Remote Similarity	NPD6847	Approved
0.605	Remote Similarity	NPD6617	Approved
0.605	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8130	Phase 1
0.605	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6929	Approved
0.6032	Remote Similarity	NPD7604	Phase 2
0.6019	Remote Similarity	NPD5692	Phase 3
0.6019	Remote Similarity	NPD4096	Approved
0.6018	Remote Similarity	NPD6648	Approved
0.6017	Remote Similarity	NPD6014	Approved
0.6017	Remote Similarity	NPD6012	Approved
0.6017	Remote Similarity	NPD6013	Approved
0.6016	Remote Similarity	NPD7641	Discontinued
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD7901	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