NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	428.22
Volume:	437.733
LogP:	4.922
LogD:	3.685
LogS:	-3.751
# Rotatable Bonds:	1
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	4.427
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.171
MDCK Permeability:	2.795820910250768e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.69

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	90.89154815673828%
Volume Distribution (VD):	1.425
Pgp-substrate:	8.040675163269043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.723
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.421
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	11.696
Half-life (T1/2):	0.233

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.588
Maximum Recommended Daily Dose:	0.427
Skin Sensitization:	0.195
Carcinogencity:	0.247
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC477676

Natural Product ID:	NPC477676
*Common Name:**	IPIYDMBLPWQZGB-MZXZQTHYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IPIYDMBLPWQZGB-MZXZQTHYSA-N
Standard InCHI:	InChI=1S/C25H32O6/c1-13-15-12-29-22(27)19(15)21(28-6)14-11-17-24(4)9-8-18(26)30-23(2,3)16(24)7-10-25(17,5)31-20(13)14/h16-17H,7-12H2,1-6H3/t16-,17+,24-,25-/m0/s1
SMILES:	Cc1c2COC(=O)c2c(c2C[C@@H]3[C@@]4(C)CCC(=O)OC(C)(C)[C@@H]4CC[C@]3(C)Oc12)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3310796
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO40273	Penicillium rudallense	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31710223]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	3
Others	1

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	<	10000.0	nM	PMID[513035]
NPT27	Others	Unspecified		IC50	<	10000.0	nM	PMID[513035]
NPT2	Others	Unspecified		Inhibition	=	36.3	%	PMID[513035]
NPT2	Others	Unspecified		IC50	=	10.0	nM	PMID[513035]
NPT2	Others	Unspecified		ED50	=	1.9	uM	PMID[513036]

☑ 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 NPC477676 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	439
0.1-0.2	1850
0.2-0.3	3658
0.3-0.4	8336
0.4-0.5	10872
0.5-0.6	5458
0.6-0.7	7263
0.7-0.8	4675
0.8-0.85	130
0.85-0.9	3
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9662	High Similarity	NPC477675
0.9658	High Similarity	NPC477673
0.9658	High Similarity	NPC477672
0.9527	High Similarity	NPC477669
0.9463	High Similarity	NPC477687
0.9463	High Similarity	NPC477671
0.94	High Similarity	NPC477674
0.8758	High Similarity	NPC477670
0.8662	High Similarity	NPC239118
0.8645	High Similarity	NPC472799
0.8609	High Similarity	NPC75694
0.8599	High Similarity	NPC158542
0.8571	High Similarity	NPC125465
0.8562	High Similarity	NPC470359
0.8553	High Similarity	NPC470357
0.8544	High Similarity	NPC4950
0.8535	High Similarity	NPC4547
0.8497	Intermediate Similarity	NPC137296
0.8497	Intermediate Similarity	NPC8817
0.8497	Intermediate Similarity	NPC245757
0.8497	Intermediate Similarity	NPC304351
0.8462	Intermediate Similarity	NPC217447
0.8462	Intermediate Similarity	NPC271681
0.8452	Intermediate Similarity	NPC474660
0.8452	Intermediate Similarity	NPC150928
0.8447	Intermediate Similarity	NPC100849
0.8431	Intermediate Similarity	NPC473927
0.8428	Intermediate Similarity	NPC218818
0.8421	Intermediate Similarity	NPC470932
0.8395	Intermediate Similarity	NPC314653
0.8395	Intermediate Similarity	NPC316262
0.8385	Intermediate Similarity	NPC473022
0.8365	Intermediate Similarity	NPC272196
0.8344	Intermediate Similarity	NPC472621
0.8344	Intermediate Similarity	NPC469818
0.8344	Intermediate Similarity	NPC273483
0.8333	Intermediate Similarity	NPC119929
0.8333	Intermediate Similarity	NPC473466
0.8323	Intermediate Similarity	NPC472661
0.8313	Intermediate Similarity	NPC472617
0.8313	Intermediate Similarity	NPC474373
0.8303	Intermediate Similarity	NPC477573
0.8303	Intermediate Similarity	NPC477571
0.8303	Intermediate Similarity	NPC477572
0.8302	Intermediate Similarity	NPC146211
0.8302	Intermediate Similarity	NPC470625
0.8301	Intermediate Similarity	NPC189650
0.8293	Intermediate Similarity	NPC472622
0.8282	Intermediate Similarity	NPC102372
0.828	Intermediate Similarity	NPC473131
0.828	Intermediate Similarity	NPC470675
0.828	Intermediate Similarity	NPC473732
0.828	Intermediate Similarity	NPC478148
0.8269	Intermediate Similarity	NPC291049
0.8269	Intermediate Similarity	NPC233267
0.8263	Intermediate Similarity	NPC294149
0.8261	Intermediate Similarity	NPC470810
0.8255	Intermediate Similarity	NPC156967
0.8255	Intermediate Similarity	NPC472599
0.8253	Intermediate Similarity	NPC472620
0.825	Intermediate Similarity	NPC196448
0.8247	Intermediate Similarity	NPC294365
0.8247	Intermediate Similarity	NPC117716
0.8247	Intermediate Similarity	NPC470674
0.8247	Intermediate Similarity	NPC470673
0.8235	Intermediate Similarity	NPC471643
0.8235	Intermediate Similarity	NPC472344
0.8235	Intermediate Similarity	NPC475656
0.8235	Intermediate Similarity	NPC471639
0.8235	Intermediate Similarity	NPC475148
0.8228	Intermediate Similarity	NPC87708
0.8228	Intermediate Similarity	NPC477960
0.8228	Intermediate Similarity	NPC477961
0.8228	Intermediate Similarity	NPC477962
0.8228	Intermediate Similarity	NPC475116
0.8221	Intermediate Similarity	NPC29055
0.8221	Intermediate Similarity	NPC173587
0.8221	Intermediate Similarity	NPC208120
0.8217	Intermediate Similarity	NPC202595
0.8217	Intermediate Similarity	NPC158866
0.8214	Intermediate Similarity	NPC324220
0.8214	Intermediate Similarity	NPC312630
0.8205	Intermediate Similarity	NPC105415
0.8205	Intermediate Similarity	NPC37139
0.8205	Intermediate Similarity	NPC472345
0.82	Intermediate Similarity	NPC245058
0.82	Intermediate Similarity	NPC470983
0.82	Intermediate Similarity	NPC470982
0.8193	Intermediate Similarity	NPC17219
0.8193	Intermediate Similarity	NPC313717
0.8193	Intermediate Similarity	NPC315306
0.8182	Intermediate Similarity	NPC184702
0.8182	Intermediate Similarity	NPC232936
0.8176	Intermediate Similarity	NPC210942
0.8176	Intermediate Similarity	NPC169990
0.8171	Intermediate Similarity	NPC21016
0.8171	Intermediate Similarity	NPC146584
0.817	Intermediate Similarity	NPC297985
0.817	Intermediate Similarity	NPC201820
0.817	Intermediate Similarity	NPC111201
0.8165	Intermediate Similarity	NPC133856
0.8165	Intermediate Similarity	NPC149526
0.8165	Intermediate Similarity	NPC72958
0.8165	Intermediate Similarity	NPC232645
0.8165	Intermediate Similarity	NPC474417
0.816	Intermediate Similarity	NPC475106
0.8155	Intermediate Similarity	NPC289147
0.8153	Intermediate Similarity	NPC471114
0.8148	Intermediate Similarity	NPC472618
0.8148	Intermediate Similarity	NPC143050
0.8148	Intermediate Similarity	NPC313368
0.8148	Intermediate Similarity	NPC470358
0.8141	Intermediate Similarity	NPC19747
0.8141	Intermediate Similarity	NPC474108
0.8141	Intermediate Similarity	NPC125801
0.8141	Intermediate Similarity	NPC177995
0.8133	Intermediate Similarity	NPC213416
0.8133	Intermediate Similarity	NPC473202
0.8133	Intermediate Similarity	NPC102810
0.8133	Intermediate Similarity	NPC472619
0.8129	Intermediate Similarity	NPC71184
0.8129	Intermediate Similarity	NPC62799
0.8129	Intermediate Similarity	NPC206212
0.8129	Intermediate Similarity	NPC49282
0.8129	Intermediate Similarity	NPC171656
0.8125	Intermediate Similarity	NPC89625
0.8125	Intermediate Similarity	NPC149618
0.8121	Intermediate Similarity	NPC472452
0.8121	Intermediate Similarity	NPC475109
0.8118	Intermediate Similarity	NPC473729
0.8118	Intermediate Similarity	NPC473607
0.8117	Intermediate Similarity	NPC167663
0.8113	Intermediate Similarity	NPC40356
0.8113	Intermediate Similarity	NPC175978
0.8113	Intermediate Similarity	NPC154683
0.811	Intermediate Similarity	NPC156082
0.811	Intermediate Similarity	NPC475055
0.8105	Intermediate Similarity	NPC82920
0.8105	Intermediate Similarity	NPC164697
0.8105	Intermediate Similarity	NPC171094
0.8105	Intermediate Similarity	NPC289660
0.8101	Intermediate Similarity	NPC179178
0.8098	Intermediate Similarity	NPC117985
0.8095	Intermediate Similarity	NPC476311
0.8089	Intermediate Similarity	NPC211625
0.8089	Intermediate Similarity	NPC145467
0.8086	Intermediate Similarity	NPC470339
0.8086	Intermediate Similarity	NPC50430
0.8077	Intermediate Similarity	NPC470676
0.8077	Intermediate Similarity	NPC473135
0.8077	Intermediate Similarity	NPC260946
0.8077	Intermediate Similarity	NPC225173
0.8077	Intermediate Similarity	NPC286038
0.8077	Intermediate Similarity	NPC473132
0.8077	Intermediate Similarity	NPC163846
0.8077	Intermediate Similarity	NPC237208
0.8075	Intermediate Similarity	NPC180924
0.8072	Intermediate Similarity	NPC76647
0.8065	Intermediate Similarity	NPC307895
0.8065	Intermediate Similarity	NPC470553
0.8063	Intermediate Similarity	NPC135522
0.8063	Intermediate Similarity	NPC273248
0.8061	Intermediate Similarity	NPC112981
0.8061	Intermediate Similarity	NPC473286
0.8059	Intermediate Similarity	NPC233978
0.8052	Intermediate Similarity	NPC469579
0.8052	Intermediate Similarity	NPC471640
0.8052	Intermediate Similarity	NPC471644
0.8052	Intermediate Similarity	NPC285659
0.8052	Intermediate Similarity	NPC205071
0.8052	Intermediate Similarity	NPC157497
0.8052	Intermediate Similarity	NPC81337
0.805	Intermediate Similarity	NPC290671
0.8049	Intermediate Similarity	NPC108767
0.8049	Intermediate Similarity	NPC472402
0.8047	Intermediate Similarity	NPC162248
0.8039	Intermediate Similarity	NPC472515
0.8039	Intermediate Similarity	NPC270913
0.8039	Intermediate Similarity	NPC473209
0.8038	Intermediate Similarity	NPC164299
0.8038	Intermediate Similarity	NPC303989
0.8038	Intermediate Similarity	NPC158338
0.8038	Intermediate Similarity	NPC288036
0.8038	Intermediate Similarity	NPC474305
0.8038	Intermediate Similarity	NPC100985
0.8038	Intermediate Similarity	NPC97029
0.8038	Intermediate Similarity	NPC97028
0.8038	Intermediate Similarity	NPC65589
0.8037	Intermediate Similarity	NPC47623
0.8037	Intermediate Similarity	NPC472055
0.8036	Intermediate Similarity	NPC118128
0.8026	Intermediate Similarity	NPC38153
0.8025	Intermediate Similarity	NPC66991
0.8025	Intermediate Similarity	NPC282335
0.8025	Intermediate Similarity	NPC308200
0.8025	Intermediate Similarity	NPC164110
0.8025	Intermediate Similarity	NPC263483
0.8025	Intermediate Similarity	NPC246647
0.8025	Intermediate Similarity	NPC123153
0.8025	Intermediate Similarity	NPC212967

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 NPC477676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1115
0.2-0.3	2061
0.3-0.4	2659
0.4-0.5	1850
0.5-0.6	729
0.6-0.7	296
0.7-0.8	60
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD2533	Approved
0.8609	High Similarity	NPD2532	Approved
0.8609	High Similarity	NPD2534	Approved
0.8291	Intermediate Similarity	NPD7819	Suspended
0.8049	Intermediate Similarity	NPD5710	Approved
0.8049	Intermediate Similarity	NPD5711	Approved
0.8039	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD5494	Approved
0.7879	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD920	Approved
0.7798	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD6599	Discontinued
0.7763	Intermediate Similarity	NPD6651	Approved
0.7756	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6232	Discontinued
0.7677	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7613	Intermediate Similarity	NPD2796	Approved
0.7607	Intermediate Similarity	NPD7411	Suspended
0.7602	Intermediate Similarity	NPD5844	Phase 1
0.759	Intermediate Similarity	NPD3749	Approved
0.759	Intermediate Similarity	NPD7075	Discontinued
0.758	Intermediate Similarity	NPD1243	Approved
0.7576	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD3226	Approved
0.747	Intermediate Similarity	NPD3817	Phase 2
0.7455	Intermediate Similarity	NPD6801	Discontinued
0.7438	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7436	Intermediate Similarity	NPD3748	Approved
0.7425	Intermediate Similarity	NPD7768	Phase 2
0.7391	Intermediate Similarity	NPD6799	Approved
0.7371	Intermediate Similarity	NPD6559	Discontinued
0.7349	Intermediate Similarity	NPD1934	Approved
0.7346	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD919	Approved
0.7326	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD7985	Registered
0.7273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7644	Approved
0.7229	Intermediate Similarity	NPD4380	Phase 2
0.7219	Intermediate Similarity	NPD3882	Suspended
0.7205	Intermediate Similarity	NPD4628	Phase 3
0.7205	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD1465	Phase 2
0.7202	Intermediate Similarity	NPD2801	Approved
0.7198	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1551	Phase 2
0.717	Intermediate Similarity	NPD2935	Discontinued
0.7169	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7118	Intermediate Similarity	NPD4966	Approved
0.7115	Intermediate Similarity	NPD8032	Phase 2
0.7107	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1510	Phase 2
0.7102	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7286	Phase 2
0.7101	Intermediate Similarity	NPD5760	Phase 2
0.7101	Intermediate Similarity	NPD5761	Phase 2
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7091	Intermediate Similarity	NPD6273	Approved
0.7089	Intermediate Similarity	NPD1607	Approved
0.7076	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1511	Approved
0.707	Intermediate Similarity	NPD2979	Phase 3
0.7069	Intermediate Similarity	NPD3926	Phase 2
0.7062	Intermediate Similarity	NPD7074	Phase 3
0.7059	Intermediate Similarity	NPD5402	Approved
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7051	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6234	Discontinued
0.7029	Intermediate Similarity	NPD6166	Phase 2
0.7029	Intermediate Similarity	NPD2403	Approved
0.7029	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7003	Approved
0.6988	Remote Similarity	NPD1512	Approved
0.6982	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7390	Discontinued
0.6968	Remote Similarity	NPD8285	Discontinued
0.6966	Remote Similarity	NPD7472	Approved
0.6964	Remote Similarity	NPD7458	Discontinued
0.6962	Remote Similarity	NPD1240	Approved
0.6949	Remote Similarity	NPD7228	Approved
0.6944	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5691	Approved
0.6927	Remote Similarity	NPD5953	Discontinued
0.6927	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1471	Phase 3
0.6914	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1281	Approved
0.689	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7251	Discontinued
0.6887	Remote Similarity	NPD17	Approved
0.6887	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8150	Discontinued
0.6879	Remote Similarity	NPD4625	Phase 3
0.686	Remote Similarity	NPD5353	Approved
0.6855	Remote Similarity	NPD4307	Phase 2
0.6852	Remote Similarity	NPD5408	Approved
0.6852	Remote Similarity	NPD5405	Approved
0.6852	Remote Similarity	NPD2438	Suspended
0.6852	Remote Similarity	NPD5406	Approved
0.6852	Remote Similarity	NPD5404	Approved
0.6851	Remote Similarity	NPD7808	Phase 3
0.6845	Remote Similarity	NPD5403	Approved
0.6837	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7783	Phase 2
0.6833	Remote Similarity	NPD6797	Phase 2
0.6829	Remote Similarity	NPD2654	Approved
0.6826	Remote Similarity	NPD5401	Approved
0.6823	Remote Similarity	NPD7435	Discontinued
0.6821	Remote Similarity	NPD8151	Discontinued
0.6811	Remote Similarity	NPD4287	Approved
0.6811	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7240	Approved
0.679	Remote Similarity	NPD7033	Discontinued
0.6782	Remote Similarity	NPD8366	Approved
0.6774	Remote Similarity	NPD1283	Approved
0.6774	Remote Similarity	NPD6696	Suspended
0.6761	Remote Similarity	NPD8127	Discontinued
0.676	Remote Similarity	NPD7177	Discontinued
0.6753	Remote Similarity	NPD3972	Approved
0.6753	Remote Similarity	NPD1608	Approved
0.6748	Remote Similarity	NPD4476	Approved
0.6748	Remote Similarity	NPD4477	Approved
0.6748	Remote Similarity	NPD2531	Phase 2
0.6733	Remote Similarity	NPD7340	Approved
0.6731	Remote Similarity	NPD3267	Approved
0.6731	Remote Similarity	NPD3266	Approved
0.673	Remote Similarity	NPD1296	Phase 2
0.673	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3764	Approved
0.6727	Remote Similarity	NPD6674	Discontinued
0.6723	Remote Similarity	NPD3787	Discontinued
0.671	Remote Similarity	NPD4749	Approved
0.6708	Remote Similarity	NPD1933	Approved
0.6708	Remote Similarity	NPD230	Phase 1
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2344	Approved
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1019	Discontinued
0.6688	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4308	Phase 3
0.6686	Remote Similarity	NPD5889	Approved
0.6686	Remote Similarity	NPD5890	Approved
0.6685	Remote Similarity	NPD5242	Approved
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD4288	Approved
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.665	Remote Similarity	NPD8491	Approved
0.6649	Remote Similarity	NPD7697	Approved
0.6649	Remote Similarity	NPD7696	Phase 3

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