NPASS Compound

Structure

NPC60848 OpenBabel07101718312D 23 27 0 0 0 0 0 0 0 0999 V2000 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1915 3.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 3.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7847 4.7872 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 -1.8171 1.1910 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 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 3.1691 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7902 4.8917 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 4.0827 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 3.0000 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 1.3835 5.8052 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 0.2079 3.9781 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 14 1 0 0 0 0 11 15 2 0 0 0 0 12 15 1 0 0 0 0 12 17 2 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.09
Volume:	308.467
LogP:	5.369
LogD:	4.276
LogS:	-4.77
# Rotatable Bonds:	0
TPSA:	55.74
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.247
Fsp3:	0.158
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:	-4.853
MDCK Permeability:	2.119134478562046e-05
Pgp-inhibitor:	0.42
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.33440399169922%
Volume Distribution (VD):	0.465
Pgp-substrate:	9.448318481445312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.883
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.873
CYP2C9-substrate:	0.753
CYP2D6-inhibitor:	0.381
CYP2D6-substrate:	0.511
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	8.717
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.375
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.642
Skin Sensitization:	0.523
Carcinogencity:	0.924
Eye Corrosion:	0.003
Eye Irritation:	0.114
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC60848

Natural Product ID:	NPC60848
*Common Name:**	Paucinervin C
IUPAC Name:	n.a.
Synonyms:	Paucinervin C
Standard InCHIKey:	ZSMMKJRUHRQXAJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H14O4/c1-19(2)8-6-11-14-10-4-3-5-13(20)16(10)22-18(14)17-12(7-9-21-17)15(11)23-19/h3-9,20H,1-2H3
SMILES:	Oc1cccc2c1oc1c2c2C=CC(Oc2c2c1occ2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1254022
PubChem CID:	52943692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20594858]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	52500.0	nM	PMID[527908]

☑ 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 NPC60848 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	487
0.1-0.2	2107
0.2-0.3	4697
0.3-0.4	11679
0.4-0.5	6269
0.5-0.6	4184
0.6-0.7	5619
0.7-0.8	5357
0.8-0.85	1634
0.85-0.9	631
0.9-0.95	32
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9209	High Similarity	NPC471842
0.92	High Similarity	NPC49667
0.92	High Similarity	NPC8127
0.9143	High Similarity	NPC287243
0.9138	High Similarity	NPC230619
0.9138	High Similarity	NPC54098
0.9101	High Similarity	NPC228209
0.9086	High Similarity	NPC82217
0.9086	High Similarity	NPC216842
0.9086	High Similarity	NPC65885
0.9086	High Similarity	NPC476640
0.9086	High Similarity	NPC277510
0.9075	High Similarity	NPC241820
0.904	High Similarity	NPC23553
0.904	High Similarity	NPC77179
0.9034	High Similarity	NPC227906
0.8994	High Similarity	NPC8927
0.8989	High Similarity	NPC104682
0.8983	High Similarity	NPC471841
0.8977	High Similarity	NPC310794
0.8971	High Similarity	NPC476641
0.8966	High Similarity	NPC470704
0.896	High Similarity	NPC38914
0.8956	High Similarity	NPC295436
0.895	High Similarity	NPC240808
0.8944	High Similarity	NPC71260
0.8933	High Similarity	NPC221820
0.8902	High Similarity	NPC59295
0.8902	High Similarity	NPC1706
0.8902	High Similarity	NPC1755
0.8902	High Similarity	NPC263092
0.8902	High Similarity	NPC39305
0.8889	High Similarity	NPC246153
0.8889	High Similarity	NPC240508
0.8876	High Similarity	NPC24258
0.887	High Similarity	NPC117450
0.887	High Similarity	NPC233956
0.8864	High Similarity	NPC131866
0.8864	High Similarity	NPC28042
0.8857	High Similarity	NPC247973
0.8851	High Similarity	NPC36320
0.8851	High Similarity	NPC45449
0.8844	High Similarity	NPC193998
0.8844	High Similarity	NPC294965
0.8844	High Similarity	NPC238995
0.8827	High Similarity	NPC98546
0.8827	High Similarity	NPC246877
0.882	High Similarity	NPC245975
0.8814	High Similarity	NPC28589
0.8814	High Similarity	NPC248593
0.8807	High Similarity	NPC247136
0.8807	High Similarity	NPC202470
0.88	High Similarity	NPC277480
0.8793	High Similarity	NPC65846
0.8793	High Similarity	NPC133065
0.8793	High Similarity	NPC270837
0.8786	High Similarity	NPC188486
0.8786	High Similarity	NPC264293
0.8778	High Similarity	NPC476273
0.8764	High Similarity	NPC62640
0.8757	High Similarity	NPC281835
0.875	High Similarity	NPC95715
0.875	High Similarity	NPC50394
0.8743	High Similarity	NPC39306
0.8743	High Similarity	NPC37183
0.8736	High Similarity	NPC272722
0.8736	High Similarity	NPC219861
0.8736	High Similarity	NPC476170
0.8736	High Similarity	NPC312056
0.8736	High Similarity	NPC84515
0.8729	High Similarity	NPC475996
0.8722	High Similarity	NPC297807
0.8715	High Similarity	NPC289244
0.8708	High Similarity	NPC174700
0.8708	High Similarity	NPC157522
0.8693	High Similarity	NPC170245
0.8693	High Similarity	NPC37870
0.8693	High Similarity	NPC53640
0.8686	High Similarity	NPC101769
0.8686	High Similarity	NPC472582
0.8678	High Similarity	NPC66288
0.8678	High Similarity	NPC258331
0.8678	High Similarity	NPC304387
0.8674	High Similarity	NPC183843
0.8671	High Similarity	NPC16935
0.8671	High Similarity	NPC196879
0.8667	High Similarity	NPC107244
0.8659	High Similarity	NPC473834
0.8659	High Similarity	NPC30550
0.8644	High Similarity	NPC186392
0.8636	High Similarity	NPC239752
0.8636	High Similarity	NPC303174
0.8636	High Similarity	NPC326520
0.8636	High Similarity	NPC291110
0.8636	High Similarity	NPC300053
0.8636	High Similarity	NPC472450
0.8636	High Similarity	NPC275780
0.8629	High Similarity	NPC81679
0.8626	High Similarity	NPC47883
0.8621	High Similarity	NPC476980
0.8621	High Similarity	NPC246478
0.8611	High Similarity	NPC290304
0.8611	High Similarity	NPC53917
0.8611	High Similarity	NPC66804
0.8611	High Similarity	NPC236327
0.8611	High Similarity	NPC224165
0.8596	High Similarity	NPC152477
0.8596	High Similarity	NPC41853
0.8588	High Similarity	NPC43319
0.8588	High Similarity	NPC39091
0.858	High Similarity	NPC475985
0.858	High Similarity	NPC470459
0.858	High Similarity	NPC207690
0.858	High Similarity	NPC197168
0.858	High Similarity	NPC472581
0.858	High Similarity	NPC236132
0.858	High Similarity	NPC23298
0.858	High Similarity	NPC41301
0.858	High Similarity	NPC109180
0.858	High Similarity	NPC189473
0.8571	High Similarity	NPC61010
0.8571	High Similarity	NPC311740
0.8571	High Similarity	NPC113446
0.8564	High Similarity	NPC156955
0.8563	High Similarity	NPC195832
0.8563	High Similarity	NPC250076
0.8563	High Similarity	NPC228501
0.8563	High Similarity	NPC55738
0.8555	High Similarity	NPC245546
0.8555	High Similarity	NPC266960
0.8555	High Similarity	NPC45131
0.8555	High Similarity	NPC472461
0.8555	High Similarity	NPC43243
0.8547	High Similarity	NPC472276
0.8547	High Similarity	NPC190351
0.8547	High Similarity	NPC101107
0.8547	High Similarity	NPC109827
0.8547	High Similarity	NPC124470
0.8539	High Similarity	NPC150131
0.8539	High Similarity	NPC158761
0.8539	High Similarity	NPC476459
0.8539	High Similarity	NPC167479
0.8539	High Similarity	NPC218226
0.8539	High Similarity	NPC126204
0.8531	High Similarity	NPC25361
0.8531	High Similarity	NPC470457
0.8523	High Similarity	NPC329760
0.8523	High Similarity	NPC472448
0.8523	High Similarity	NPC261470
0.8523	High Similarity	NPC229632
0.8523	High Similarity	NPC83922
0.8514	High Similarity	NPC220582
0.8514	High Similarity	NPC56085
0.8514	High Similarity	NPC14353
0.8514	High Similarity	NPC139036
0.8514	High Similarity	NPC328102
0.8514	High Similarity	NPC228785
0.8514	High Similarity	NPC304839
0.8514	High Similarity	NPC84571
0.8508	High Similarity	NPC289147
0.8508	High Similarity	NPC139350
0.8506	High Similarity	NPC268360
0.8506	High Similarity	NPC287979
0.8506	High Similarity	NPC163524
0.8506	High Similarity	NPC110070
0.8506	High Similarity	NPC164110
0.8506	High Similarity	NPC305663
0.8506	High Similarity	NPC203891
0.8506	High Similarity	NPC101830
0.8506	High Similarity	NPC476981
0.8506	High Similarity	NPC246647
0.8506	High Similarity	NPC176665
0.8506	High Similarity	NPC212967
0.8506	High Similarity	NPC96342
0.85	High Similarity	NPC292794
0.85	High Similarity	NPC307286
0.85	High Similarity	NPC260263
0.85	High Similarity	NPC121333
0.8497	Intermediate Similarity	NPC39184
0.8497	Intermediate Similarity	NPC26227
0.8497	Intermediate Similarity	NPC233776
0.8497	Intermediate Similarity	NPC44079
0.8497	Intermediate Similarity	NPC201451
0.8492	Intermediate Similarity	NPC165979
0.8492	Intermediate Similarity	NPC288813
0.8492	Intermediate Similarity	NPC211309
0.8492	Intermediate Similarity	NPC475805
0.8492	Intermediate Similarity	NPC165456
0.8492	Intermediate Similarity	NPC163130
0.8492	Intermediate Similarity	NPC476637
0.8492	Intermediate Similarity	NPC242395
0.8486	Intermediate Similarity	NPC226725
0.8483	Intermediate Similarity	NPC477517
0.8483	Intermediate Similarity	NPC470462
0.8483	Intermediate Similarity	NPC67450
0.8483	Intermediate Similarity	NPC193881
0.8483	Intermediate Similarity	NPC191012
0.8483	Intermediate Similarity	NPC235610
0.8483	Intermediate Similarity	NPC472449
0.8483	Intermediate Similarity	NPC119589

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 NPC60848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	448
0.1-0.2	1052
0.2-0.3	1920
0.3-0.4	2821
0.4-0.5	1657
0.5-0.6	831
0.6-0.7	289
0.7-0.8	107
0.8-0.85	22
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8786	High Similarity	NPD1247	Approved
0.8448	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD2801	Approved
0.8249	Intermediate Similarity	NPD919	Approved
0.8171	Intermediate Similarity	NPD1934	Approved
0.8125	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6232	Discontinued
0.8101	Intermediate Similarity	NPD5494	Approved
0.8087	Intermediate Similarity	NPD5844	Phase 1
0.8077	Intermediate Similarity	NPD7473	Discontinued
0.8054	Intermediate Similarity	NPD6559	Discontinued
0.8035	Intermediate Similarity	NPD1512	Approved
0.8033	Intermediate Similarity	NPD3818	Discontinued
0.8022	Intermediate Similarity	NPD6166	Phase 2
0.8022	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD3817	Phase 2
0.7919	Intermediate Similarity	NPD1511	Approved
0.7914	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3749	Approved
0.7874	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD6959	Discontinued
0.779	Intermediate Similarity	NPD7075	Discontinued
0.776	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6797	Phase 2
0.7684	Intermediate Similarity	NPD920	Approved
0.7672	Intermediate Similarity	NPD7251	Discontinued
0.7667	Intermediate Similarity	NPD6801	Discontinued
0.7656	Intermediate Similarity	NPD8434	Phase 2
0.7654	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD6599	Discontinued
0.7637	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7808	Phase 3
0.7624	Intermediate Similarity	NPD1465	Phase 2
0.7624	Intermediate Similarity	NPD7819	Suspended
0.7606	Intermediate Similarity	NPD7054	Approved
0.759	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5402	Approved
0.7571	Intermediate Similarity	NPD2533	Approved
0.7571	Intermediate Similarity	NPD2534	Approved
0.7571	Intermediate Similarity	NPD2532	Approved
0.7571	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7472	Approved
0.7566	Intermediate Similarity	NPD7074	Phase 3
0.754	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD7411	Suspended
0.7513	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.7487	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3751	Discontinued
0.7459	Intermediate Similarity	NPD6234	Discontinued
0.7458	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD1510	Phase 2
0.7429	Intermediate Similarity	NPD1549	Phase 2
0.7405	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2344	Approved
0.7371	Intermediate Similarity	NPD1471	Phase 3
0.7371	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7768	Phase 2
0.7341	Intermediate Similarity	NPD1607	Approved
0.7327	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD2796	Approved
0.7288	Intermediate Similarity	NPD2800	Approved
0.7288	Intermediate Similarity	NPD1243	Approved
0.7287	Intermediate Similarity	NPD7199	Phase 2
0.7258	Intermediate Similarity	NPD4966	Approved
0.7258	Intermediate Similarity	NPD4967	Phase 2
0.7258	Intermediate Similarity	NPD4965	Approved
0.7257	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3787	Discontinued
0.7247	Intermediate Similarity	NPD3750	Approved
0.7243	Intermediate Similarity	NPD7907	Approved
0.7241	Intermediate Similarity	NPD6777	Approved
0.7241	Intermediate Similarity	NPD6776	Approved
0.7241	Intermediate Similarity	NPD6782	Approved
0.7241	Intermediate Similarity	NPD6779	Approved
0.7241	Intermediate Similarity	NPD6780	Approved
0.7241	Intermediate Similarity	NPD6778	Approved
0.7241	Intermediate Similarity	NPD6781	Approved
0.7232	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1240	Approved
0.7225	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD7390	Discontinued
0.722	Intermediate Similarity	NPD7435	Discontinued
0.7216	Intermediate Similarity	NPD1551	Phase 2
0.7207	Intermediate Similarity	NPD2309	Approved
0.7198	Intermediate Similarity	NPD5403	Approved
0.7191	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7228	Approved
0.7182	Intermediate Similarity	NPD5401	Approved
0.7175	Intermediate Similarity	NPD2346	Discontinued
0.715	Intermediate Similarity	NPD4111	Phase 1
0.715	Intermediate Similarity	NPD4665	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7121	Intermediate Similarity	NPD8150	Discontinued
0.7119	Intermediate Similarity	NPD2935	Discontinued
0.7104	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7870	Phase 2
0.7101	Intermediate Similarity	NPD7871	Phase 2
0.7097	Intermediate Similarity	NPD37	Approved
0.709	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5710	Approved
0.7068	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD5761	Phase 2
0.7059	Intermediate Similarity	NPD5760	Phase 2
0.7053	Intermediate Similarity	NPD7696	Phase 3
0.7053	Intermediate Similarity	NPD7698	Approved
0.7053	Intermediate Similarity	NPD7697	Approved
0.705	Intermediate Similarity	NPD4287	Approved
0.7017	Intermediate Similarity	NPD6190	Approved
0.7014	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7874	Approved
0.701	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7701	Phase 2
0.6995	Remote Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD6534	Approved
0.6995	Remote Similarity	NPD2403	Approved
0.6989	Remote Similarity	NPD230	Phase 1
0.6981	Remote Similarity	NPD7783	Phase 2
0.6981	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7229	Phase 3
0.6967	Remote Similarity	NPD8151	Discontinued
0.6966	Remote Similarity	NPD3748	Approved
0.6961	Remote Similarity	NPD4628	Phase 3
0.694	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD9494	Approved
0.6932	Remote Similarity	NPD1613	Approved
0.6932	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6100	Approved
0.6927	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6099	Approved
0.6923	Remote Similarity	NPD2163	Approved
0.6901	Remote Similarity	NPD7801	Approved
0.6897	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7699	Phase 2
0.6893	Remote Similarity	NPD7700	Phase 2
0.6893	Remote Similarity	NPD447	Suspended
0.6875	Remote Similarity	NPD2494	Approved
0.6875	Remote Similarity	NPD2493	Approved
0.6869	Remote Similarity	NPD6764	Approved
0.6869	Remote Similarity	NPD6765	Approved
0.6857	Remote Similarity	NPD4625	Phase 3
0.6845	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6823	Phase 2
0.6842	Remote Similarity	NPD3057	Approved
0.6839	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5405	Approved
0.6833	Remote Similarity	NPD5404	Approved
0.6833	Remote Similarity	NPD5406	Approved
0.6833	Remote Similarity	NPD5408	Approved
0.6818	Remote Similarity	NPD2313	Discontinued
0.6818	Remote Similarity	NPD5953	Discontinued
0.6802	Remote Similarity	NPD7286	Phase 2
0.6794	Remote Similarity	NPD3452	Approved
0.6794	Remote Similarity	NPD3450	Approved
0.6791	Remote Similarity	NPD1653	Approved
0.6787	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7685	Pre-registration
0.6784	Remote Similarity	NPD7240	Approved
0.6778	Remote Similarity	NPD2799	Discontinued
0.6777	Remote Similarity	NPD4583	Approved
0.6777	Remote Similarity	NPD4582	Approved
0.6776	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD2972	Approved
0.6762	Remote Similarity	NPD2491	Approved
0.6762	Remote Similarity	NPD3533	Approved
0.6761	Remote Similarity	NPD3027	Phase 3
0.6754	Remote Similarity	NPD7048	Phase 3
0.6754	Remote Similarity	NPD2296	Approved
0.6751	Remote Similarity	NPD7177	Discontinued
0.6742	Remote Similarity	NPD4060	Phase 1
0.6733	Remote Similarity	NPD6784	Approved
0.6733	Remote Similarity	NPD6785	Approved
0.673	Remote Similarity	NPD4004	Approved
0.673	Remote Similarity	NPD4002	Approved
0.6723	Remote Similarity	NPD3764	Approved
0.672	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8319	Approved
0.6698	Remote Similarity	NPD8320	Phase 1
0.6697	Remote Similarity	NPD7047	Phase 3
0.6683	Remote Similarity	NPD2974	Approved
0.6683	Remote Similarity	NPD2973	Approved
0.6683	Remote Similarity	NPD2975	Approved
0.6682	Remote Similarity	NPD3448	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