NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	264.305
LogP:	2.764
LogD:	2.818
LogS:	-3.46
# Rotatable Bonds:	0
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	4.567
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.003
MDCK Permeability:	1.2925158443977125e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.92
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	92.4043197631836%
Volume Distribution (VD):	1.497
Pgp-substrate:	10.618677139282227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.338
CYP2C9-substrate:	0.395
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.259
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	7.514
Half-life (T1/2):	0.815

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.707
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.765
Carcinogencity:	0.905
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC175617

Natural Product ID:	NPC175617
*Common Name:**	(+)-Pseudodeflectusin
IUPAC Name:	(7R,9S)-9-hydroxy-7-methyl-2-propan-2-ylidene-7,9-dihydro-6H-furo[3,2-h]isochromen-3-one
Synonyms:
Standard InCHIKey:	LSQCSEQTJDZMSO-GLEZIHRCSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-7(2)13-12(16)10-5-4-9-6-8(3)18-15(17)11(9)14(10)19-13/h4-5,8,15,17H,6H2,1-3H3/t8-,15+/m1/s1
SMILES:	C[C@H]1O[C@H](O)c2c(C1)ccc1c2OC(=C(C)C)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419841
PubChem CID:	24763831
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO27058	Aspergillus ustus	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
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
NPT393	Cell Line	HCT-116	Homo sapiens	FC	=	2.0	n.a.	PMID[558450]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5000.0	nM	PMID[558450]

☑ 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 NPC175617 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	363
0.1-0.2	1397
0.2-0.3	3088
0.3-0.4	7822
0.4-0.5	11267
0.5-0.6	4014
0.6-0.7	6918
0.7-0.8	7301
0.8-0.85	503
0.85-0.9	14
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC471349
0.9931	High Similarity	NPC471347
0.9521	High Similarity	NPC219560
0.9514	High Similarity	NPC469385
0.9456	High Similarity	NPC471348
0.9456	High Similarity	NPC469416
0.9456	High Similarity	NPC228906
0.9189	High Similarity	NPC469425
0.8993	High Similarity	NPC471346
0.8844	High Similarity	NPC477537
0.8759	High Similarity	NPC217914
0.8716	High Similarity	NPC477535
0.8679	High Similarity	NPC216752
0.8645	High Similarity	NPC473967
0.859	High Similarity	NPC470331
0.8562	High Similarity	NPC212099
0.8562	High Similarity	NPC101116
0.8562	High Similarity	NPC278329
0.8562	High Similarity	NPC146837
0.8553	High Similarity	NPC313368
0.8553	High Similarity	NPC474630
0.8545	High Similarity	NPC470667
0.8514	High Similarity	NPC477534
0.8457	Intermediate Similarity	NPC178281
0.8452	Intermediate Similarity	NPC104172
0.8452	Intermediate Similarity	NPC88886
0.8442	Intermediate Similarity	NPC471734
0.8442	Intermediate Similarity	NPC71055
0.8434	Intermediate Similarity	NPC186800
0.8421	Intermediate Similarity	NPC469885
0.8415	Intermediate Similarity	NPC191653
0.8415	Intermediate Similarity	NPC473202
0.8405	Intermediate Similarity	NPC178851
0.84	Intermediate Similarity	NPC477408
0.8397	Intermediate Similarity	NPC325983
0.8383	Intermediate Similarity	NPC475233
0.8377	Intermediate Similarity	NPC471735
0.8373	Intermediate Similarity	NPC98776
0.8373	Intermediate Similarity	NPC85368
0.8367	Intermediate Similarity	NPC477536
0.8366	Intermediate Similarity	NPC477409
0.8356	Intermediate Similarity	NPC324488
0.8354	Intermediate Similarity	NPC301233
0.8354	Intermediate Similarity	NPC63470
0.8344	Intermediate Similarity	NPC316262
0.8344	Intermediate Similarity	NPC72958
0.8344	Intermediate Similarity	NPC314653
0.8344	Intermediate Similarity	NPC232645
0.8344	Intermediate Similarity	NPC318424
0.8333	Intermediate Similarity	NPC98395
0.8323	Intermediate Similarity	NPC470358
0.8323	Intermediate Similarity	NPC306978
0.8313	Intermediate Similarity	NPC5029
0.8313	Intermediate Similarity	NPC271385
0.8313	Intermediate Similarity	NPC111536
0.8313	Intermediate Similarity	NPC473282
0.8313	Intermediate Similarity	NPC76128
0.8313	Intermediate Similarity	NPC30432
0.8313	Intermediate Similarity	NPC217602
0.8313	Intermediate Similarity	NPC104380
0.8303	Intermediate Similarity	NPC259905
0.8291	Intermediate Similarity	NPC271681
0.8291	Intermediate Similarity	NPC87708
0.8282	Intermediate Similarity	NPC17432
0.828	Intermediate Similarity	NPC202595
0.8278	Intermediate Similarity	NPC268691
0.8274	Intermediate Similarity	NPC475246
0.8272	Intermediate Similarity	NPC472780
0.8272	Intermediate Similarity	NPC269117
0.8272	Intermediate Similarity	NPC472783
0.8263	Intermediate Similarity	NPC199357
0.8263	Intermediate Similarity	NPC203751
0.8258	Intermediate Similarity	NPC470357
0.8255	Intermediate Similarity	NPC142027
0.8255	Intermediate Similarity	NPC27407
0.8253	Intermediate Similarity	NPC313717
0.8253	Intermediate Similarity	NPC315306
0.8253	Intermediate Similarity	NPC298778
0.825	Intermediate Similarity	NPC164244
0.8247	Intermediate Similarity	NPC475813
0.8239	Intermediate Similarity	NPC135522
0.8239	Intermediate Similarity	NPC193200
0.8235	Intermediate Similarity	NPC329493
0.8228	Intermediate Similarity	NPC39819
0.8224	Intermediate Similarity	NPC37206
0.8221	Intermediate Similarity	NPC125991
0.8217	Intermediate Similarity	NPC226578
0.8217	Intermediate Similarity	NPC70764
0.8214	Intermediate Similarity	NPC68381
0.8214	Intermediate Similarity	NPC3718
0.821	Intermediate Similarity	NPC472782
0.821	Intermediate Similarity	NPC472781
0.8205	Intermediate Similarity	NPC8817
0.8205	Intermediate Similarity	NPC137296
0.8199	Intermediate Similarity	NPC164110
0.8199	Intermediate Similarity	NPC96342
0.8199	Intermediate Similarity	NPC294300
0.8199	Intermediate Similarity	NPC281137
0.8199	Intermediate Similarity	NPC212967
0.8199	Intermediate Similarity	NPC282390
0.8199	Intermediate Similarity	NPC476404
0.8199	Intermediate Similarity	NPC317900
0.8199	Intermediate Similarity	NPC177742
0.8199	Intermediate Similarity	NPC246647
0.8199	Intermediate Similarity	NPC470606
0.8194	Intermediate Similarity	NPC28632
0.8193	Intermediate Similarity	NPC246274
0.8193	Intermediate Similarity	NPC470206
0.8193	Intermediate Similarity	NPC470207
0.8193	Intermediate Similarity	NPC222455
0.8187	Intermediate Similarity	NPC237560
0.8182	Intermediate Similarity	NPC471731
0.8182	Intermediate Similarity	NPC469542
0.8176	Intermediate Similarity	NPC277710
0.8176	Intermediate Similarity	NPC275878
0.8176	Intermediate Similarity	NPC273483
0.8176	Intermediate Similarity	NPC183536
0.8176	Intermediate Similarity	NPC40356
0.8176	Intermediate Similarity	NPC114257
0.8176	Intermediate Similarity	NPC34965
0.8176	Intermediate Similarity	NPC154683
0.8176	Intermediate Similarity	NPC321363
0.8176	Intermediate Similarity	NPC299149
0.8176	Intermediate Similarity	NPC253904
0.8176	Intermediate Similarity	NPC153578
0.8171	Intermediate Similarity	NPC66087
0.8171	Intermediate Similarity	NPC278419
0.8171	Intermediate Similarity	NPC179198
0.8171	Intermediate Similarity	NPC471286
0.817	Intermediate Similarity	NPC149533
0.817	Intermediate Similarity	NPC283292
0.8166	Intermediate Similarity	NPC289876
0.8166	Intermediate Similarity	NPC102053
0.8166	Intermediate Similarity	NPC46958
0.8165	Intermediate Similarity	NPC158866
0.8165	Intermediate Similarity	NPC473966
0.816	Intermediate Similarity	NPC117985
0.816	Intermediate Similarity	NPC24761
0.8155	Intermediate Similarity	NPC213052
0.8153	Intermediate Similarity	NPC215711
0.8153	Intermediate Similarity	NPC73411
0.8153	Intermediate Similarity	NPC37139
0.8153	Intermediate Similarity	NPC5537
0.8148	Intermediate Similarity	NPC470607
0.8148	Intermediate Similarity	NPC279732
0.8148	Intermediate Similarity	NPC186113
0.8141	Intermediate Similarity	NPC469758
0.8141	Intermediate Similarity	NPC300540
0.8137	Intermediate Similarity	NPC211482
0.8137	Intermediate Similarity	NPC17521
0.8137	Intermediate Similarity	NPC180924
0.8137	Intermediate Similarity	NPC154341
0.8137	Intermediate Similarity	NPC476652
0.8133	Intermediate Similarity	NPC472660
0.8133	Intermediate Similarity	NPC149244
0.8133	Intermediate Similarity	NPC48640
0.8133	Intermediate Similarity	NPC150131
0.8133	Intermediate Similarity	NPC470844
0.8129	Intermediate Similarity	NPC477860
0.8129	Intermediate Similarity	NPC151607
0.8129	Intermediate Similarity	NPC42540
0.8129	Intermediate Similarity	NPC274085
0.8129	Intermediate Similarity	NPC475161
0.8129	Intermediate Similarity	NPC471451
0.8129	Intermediate Similarity	NPC89664
0.8125	Intermediate Similarity	NPC185103
0.8125	Intermediate Similarity	NPC472799
0.8125	Intermediate Similarity	NPC210942
0.8125	Intermediate Similarity	NPC169990
0.8121	Intermediate Similarity	NPC472784
0.8118	Intermediate Similarity	NPC5671
0.8118	Intermediate Similarity	NPC47191
0.8117	Intermediate Similarity	NPC171870
0.8117	Intermediate Similarity	NPC471733
0.8117	Intermediate Similarity	NPC469579
0.8113	Intermediate Similarity	NPC471613
0.8113	Intermediate Similarity	NPC474417
0.8113	Intermediate Similarity	NPC23253
0.8113	Intermediate Similarity	NPC478148
0.8113	Intermediate Similarity	NPC258249
0.8113	Intermediate Similarity	NPC149526
0.8113	Intermediate Similarity	NPC470569
0.811	Intermediate Similarity	NPC475106
0.811	Intermediate Similarity	NPC310603
0.811	Intermediate Similarity	NPC131745
0.811	Intermediate Similarity	NPC259834
0.8107	Intermediate Similarity	NPC223735
0.8107	Intermediate Similarity	NPC307754
0.8107	Intermediate Similarity	NPC474345
0.8107	Intermediate Similarity	NPC146803
0.8105	Intermediate Similarity	NPC137009
0.8103	Intermediate Similarity	NPC205721
0.8101	Intermediate Similarity	NPC97028
0.8101	Intermediate Similarity	NPC65589
0.8101	Intermediate Similarity	NPC100985
0.8101	Intermediate Similarity	NPC288036
0.8101	Intermediate Similarity	NPC97029
0.8101	Intermediate Similarity	NPC291049
0.8101	Intermediate Similarity	NPC4423
0.8101	Intermediate Similarity	NPC77325

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 NPC175617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	904
0.2-0.3	1641
0.3-0.4	2557
0.4-0.5	2053
0.5-0.6	1101
0.6-0.7	403
0.7-0.8	170
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8155	Intermediate Similarity	NPD6559	Discontinued
0.8125	Intermediate Similarity	NPD7819	Suspended
0.8092	Intermediate Similarity	NPD2346	Discontinued
0.8077	Intermediate Similarity	NPD2534	Approved
0.8077	Intermediate Similarity	NPD2533	Approved
0.8077	Intermediate Similarity	NPD2532	Approved
0.8046	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3226	Approved
0.7976	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7075	Discontinued
0.7953	Intermediate Similarity	NPD8312	Approved
0.7953	Intermediate Similarity	NPD8313	Approved
0.7875	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6801	Discontinued
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7826	Intermediate Similarity	NPD6599	Discontinued
0.7811	Intermediate Similarity	NPD3818	Discontinued
0.7806	Intermediate Similarity	NPD1549	Phase 2
0.7805	Intermediate Similarity	NPD3882	Suspended
0.78	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7742	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD6799	Approved
0.7669	Intermediate Similarity	NPD7411	Suspended
0.7661	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD5403	Approved
0.7637	Intermediate Similarity	NPD6777	Approved
0.7637	Intermediate Similarity	NPD6778	Approved
0.7637	Intermediate Similarity	NPD6782	Approved
0.7637	Intermediate Similarity	NPD6776	Approved
0.7637	Intermediate Similarity	NPD6781	Approved
0.7637	Intermediate Similarity	NPD6779	Approved
0.7637	Intermediate Similarity	NPD6780	Approved
0.7636	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5402	Approved
0.7628	Intermediate Similarity	NPD1471	Phase 3
0.7625	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7074	Phase 3
0.7609	Intermediate Similarity	NPD7435	Discontinued
0.7607	Intermediate Similarity	NPD4380	Phase 2
0.7605	Intermediate Similarity	NPD919	Approved
0.7597	Intermediate Similarity	NPD1607	Approved
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5710	Approved
0.7574	Intermediate Similarity	NPD5711	Approved
0.7566	Intermediate Similarity	NPD411	Approved
0.7564	Intermediate Similarity	NPD2935	Discontinued
0.7564	Intermediate Similarity	NPD2796	Approved
0.756	Intermediate Similarity	NPD5494	Approved
0.7558	Intermediate Similarity	NPD7054	Approved
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2800	Approved
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD1934	Approved
0.7514	Intermediate Similarity	NPD7698	Approved
0.7514	Intermediate Similarity	NPD7472	Approved
0.7514	Intermediate Similarity	NPD7697	Approved
0.7514	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7871	Phase 2
0.7473	Intermediate Similarity	NPD7870	Phase 2
0.7468	Intermediate Similarity	NPD1240	Approved
0.7459	Intermediate Similarity	NPD6534	Approved
0.7459	Intermediate Similarity	NPD6535	Approved
0.7451	Intermediate Similarity	NPD2313	Discontinued
0.744	Intermediate Similarity	NPD3749	Approved
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3817	Phase 2
0.7423	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD1243	Approved
0.7417	Intermediate Similarity	NPD2798	Approved
0.7412	Intermediate Similarity	NPD1247	Approved
0.7405	Intermediate Similarity	NPD6002	Phase 3
0.7405	Intermediate Similarity	NPD6005	Phase 3
0.7405	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6004	Phase 3
0.7405	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7768	Phase 2
0.7375	Intermediate Similarity	NPD3750	Approved
0.7368	Intermediate Similarity	NPD6232	Discontinued
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7368	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7874	Approved
0.7362	Intermediate Similarity	NPD1512	Approved
0.7354	Intermediate Similarity	NPD7701	Phase 2
0.7351	Intermediate Similarity	NPD1203	Approved
0.7342	Intermediate Similarity	NPD6099	Approved
0.7342	Intermediate Similarity	NPD6100	Approved
0.7341	Intermediate Similarity	NPD7473	Discontinued
0.7337	Intermediate Similarity	NPD7699	Phase 2
0.7337	Intermediate Similarity	NPD7700	Phase 2
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7318	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD447	Suspended
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5762	Approved
0.7296	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2344	Approved
0.7296	Intermediate Similarity	NPD5763	Approved
0.7278	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7256	Intermediate Similarity	NPD6273	Approved
0.724	Intermediate Similarity	NPD7801	Approved
0.7239	Intermediate Similarity	NPD1511	Approved
0.7238	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1470	Approved
0.7233	Intermediate Similarity	NPD5404	Approved
0.7233	Intermediate Similarity	NPD5405	Approved
0.7233	Intermediate Similarity	NPD5406	Approved
0.7233	Intermediate Similarity	NPD5408	Approved
0.7229	Intermediate Similarity	NPD7458	Discontinued
0.7225	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7213	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6212	Phase 3
0.7213	Intermediate Similarity	NPD6213	Phase 3
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD1091	Approved
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD7177	Discontinued
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8320	Phase 1
0.7196	Intermediate Similarity	NPD8319	Approved
0.7193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1778	Approved
0.7176	Intermediate Similarity	NPD4966	Approved
0.7176	Intermediate Similarity	NPD4967	Phase 2
0.7176	Intermediate Similarity	NPD4965	Approved
0.717	Intermediate Similarity	NPD4308	Phase 3
0.717	Intermediate Similarity	NPD3748	Approved
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD2801	Approved
0.716	Intermediate Similarity	NPD5761	Phase 2
0.716	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD1608	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7117	Intermediate Similarity	NPD2309	Approved
0.7115	Intermediate Similarity	NPD3268	Approved
0.711	Intermediate Similarity	NPD7199	Phase 2
0.7102	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6674	Discontinued
0.7095	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD1933	Approved
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7076	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4626	Approved
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD8455	Phase 2
0.7059	Intermediate Similarity	NPD1283	Approved
0.7055	Intermediate Similarity	NPD7003	Approved
0.7051	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7044	Intermediate Similarity	NPD6651	Approved
0.703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9493	Approved
0.7013	Intermediate Similarity	NPD2797	Approved
0.7006	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7799	Discontinued
0.7006	Intermediate Similarity	NPD7228	Approved
0.7006	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8366	Approved
0.6994	Remote Similarity	NPD6234	Discontinued
0.6994	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5953	Discontinued
0.6981	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5124	Phase 1
0.6979	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD17	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