NPASS Compound

Structure

NPC307640 OpenBabel07101719512D 36 42 0 0 1 0 0 0 0 0999 V2000 -2.5040 -2.3731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9140 -2.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6791 -0.0579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6590 2.7031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7316 -1.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1918 0.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8065 1.1727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1918 1.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4836 0.8466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3475 -0.2215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1856 0.7494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3475 1.7282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5397 0.0973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1262 0.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -1.1964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5032 0.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2418 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9704 -0.2215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1262 -1.6838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5032 1.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9188 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8147 0.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6770 -1.1727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9704 -1.1964 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6590 -0.2215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6209 -0.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8147 1.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3541 -1.4987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8147 -1.6838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -0.2215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6590 1.7282 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9750 -1.0754 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9704 1.7282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4269 -2.4709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6590 -1.1964 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 29 1 0 0 0 0 2 29 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 12 20 2 0 0 0 0 13 21 2 0 0 0 0 14 30 1 0 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 14 1 1 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 19 15 1 6 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 23 26 2 0 0 0 0 23 28 1 0 0 0 0 24 29 1 6 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 31 1 0 0 0 0 27 33 2 0 0 0 0 28 32 1 0 0 0 0 28 34 2 0 0 0 0 29 35 1 0 0 0 0 30 3 1 1 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.22
Volume:	498.331
LogP:	6.917
LogD:	4.285
LogS:	-4.723
# Rotatable Bonds:	0
TPSA:	62.46
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	5.012
Fsp3:	0.4
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:	-4.808
MDCK Permeability:	2.9708573492825963e-05
Pgp-inhibitor:	0.102
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	97.11759185791016%
Volume Distribution (VD):	0.309
Pgp-substrate:	1.0117473602294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	4.321
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.556
AMES Toxicity:	0.554
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.087
Carcinogencity:	0.887
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.671

Download Data

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

Natural Product: NPC307640

Natural Product ID:	NPC307640
*Common Name:**	Paraensidimerin C
IUPAC Name:	n.a.
Synonyms:	Paraensidimerin C
Standard InCHIKey:	DUHDIWSVGBLULV-SUNBNRQWSA-N
Standard InCHI:	InChI=1S/C30H30N2O4/c1-29(2)24-18(22-25(35-29)16-10-6-8-12-20(16)31(4)27(22)33)14-30(3)15-19(24)23-26(36-30)17-11-7-9-13-21(17)32(5)28(23)34/h6-13,18-19,24H,14-15H2,1-5H3/t18-,19+,24-,30-/m1/s1
SMILES:	Cn1c2ccccc2c2c(c1=O)[C@H]1C[C@@]3(C)Oc4c([C@@H]([C@@H]1C(O2)(C)C)C3)c(=O)n(c1c4cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL429124
PubChem CID:	21770541
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001291] Pyranoquinolines

*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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	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
NPT2740	Cell Line	Neutrophils		IC50	>	100000.0	nM	PMID[536858]

☑ 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 NPC307640 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	607
0.1-0.2	2434
0.2-0.3	9611
0.3-0.4	8198
0.4-0.5	12136
0.5-0.6	7805
0.6-0.7	1621
0.7-0.8	275
0.8-0.85	3
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8662	High Similarity	NPC242000
0.8581	High Similarity	NPC308197
0.7871	Intermediate Similarity	NPC231382
0.7814	Intermediate Similarity	NPC471825
0.76	Intermediate Similarity	NPC469915
0.7525	Intermediate Similarity	NPC473449
0.75	Intermediate Similarity	NPC250476
0.7337	Intermediate Similarity	NPC49184
0.7337	Intermediate Similarity	NPC322621
0.7159	Intermediate Similarity	NPC320064
0.7158	Intermediate Similarity	NPC321211
0.7135	Intermediate Similarity	NPC299582
0.7127	Intermediate Similarity	NPC96901
0.7104	Intermediate Similarity	NPC186669
0.7102	Intermediate Similarity	NPC301163
0.709	Intermediate Similarity	NPC105055
0.709	Intermediate Similarity	NPC22689
0.7053	Intermediate Similarity	NPC1820
0.7021	Intermediate Similarity	NPC262725
0.701	Intermediate Similarity	NPC234933
0.701	Intermediate Similarity	NPC71124
0.6985	Remote Similarity	NPC308943
0.6974	Remote Similarity	NPC5374
0.697	Remote Similarity	NPC268077
0.6966	Remote Similarity	NPC93653
0.6957	Remote Similarity	NPC129624
0.694	Remote Similarity	NPC139085
0.694	Remote Similarity	NPC251212
0.694	Remote Similarity	NPC214626
0.6939	Remote Similarity	NPC67904
0.6939	Remote Similarity	NPC138830
0.6919	Remote Similarity	NPC207971
0.6911	Remote Similarity	NPC473569
0.6891	Remote Similarity	NPC254957
0.6869	Remote Similarity	NPC15987
0.6865	Remote Similarity	NPC264482
0.6865	Remote Similarity	NPC203202
0.6839	Remote Similarity	NPC473004
0.6837	Remote Similarity	NPC100863
0.6825	Remote Similarity	NPC97584
0.68	Remote Similarity	NPC144691
0.68	Remote Similarity	NPC87714
0.6793	Remote Similarity	NPC471604
0.6788	Remote Similarity	NPC25401
0.6786	Remote Similarity	NPC162440
0.6782	Remote Similarity	NPC207873
0.6782	Remote Similarity	NPC100573
0.6778	Remote Similarity	NPC225319
0.6778	Remote Similarity	NPC201424
0.6757	Remote Similarity	NPC276993
0.6757	Remote Similarity	NPC181138
0.6757	Remote Similarity	NPC293255
0.6757	Remote Similarity	NPC210415
0.6757	Remote Similarity	NPC298851
0.6757	Remote Similarity	NPC21752
0.6755	Remote Similarity	NPC85613
0.6754	Remote Similarity	NPC291759
0.6751	Remote Similarity	NPC17677
0.6751	Remote Similarity	NPC23080
0.6751	Remote Similarity	NPC193906
0.6748	Remote Similarity	NPC55470
0.674	Remote Similarity	NPC472117
0.6736	Remote Similarity	NPC471195
0.6736	Remote Similarity	NPC471196
0.6732	Remote Similarity	NPC10732
0.6721	Remote Similarity	NPC214960
0.6721	Remote Similarity	NPC279527
0.672	Remote Similarity	NPC190461
0.672	Remote Similarity	NPC116096
0.6719	Remote Similarity	NPC21425
0.6717	Remote Similarity	NPC241263
0.6716	Remote Similarity	NPC329833
0.6704	Remote Similarity	NPC29285
0.6702	Remote Similarity	NPC133591
0.6702	Remote Similarity	NPC6974
0.6701	Remote Similarity	NPC22476
0.67	Remote Similarity	NPC475223
0.6685	Remote Similarity	NPC315368
0.6684	Remote Similarity	NPC21483
0.6684	Remote Similarity	NPC198205
0.6683	Remote Similarity	NPC477161
0.6667	Remote Similarity	NPC5167
0.6667	Remote Similarity	NPC38823
0.6667	Remote Similarity	NPC10653
0.6667	Remote Similarity	NPC318525
0.6667	Remote Similarity	NPC246983
0.6667	Remote Similarity	NPC315051
0.6667	Remote Similarity	NPC207033
0.6667	Remote Similarity	NPC473743
0.6667	Remote Similarity	NPC113946
0.6667	Remote Similarity	NPC475448
0.6667	Remote Similarity	NPC112752
0.6667	Remote Similarity	NPC311054
0.6667	Remote Similarity	NPC472106
0.6651	Remote Similarity	NPC248601
0.6651	Remote Similarity	NPC77777
0.665	Remote Similarity	NPC159815
0.665	Remote Similarity	NPC222561
0.665	Remote Similarity	NPC305542
0.6649	Remote Similarity	NPC260075
0.6649	Remote Similarity	NPC474059
0.6648	Remote Similarity	NPC472120
0.6648	Remote Similarity	NPC472101
0.6634	Remote Similarity	NPC25961
0.6633	Remote Similarity	NPC103230
0.663	Remote Similarity	NPC472114
0.663	Remote Similarity	NPC472115
0.662	Remote Similarity	NPC470631
0.662	Remote Similarity	NPC35390
0.662	Remote Similarity	NPC473781
0.6618	Remote Similarity	NPC285192
0.6618	Remote Similarity	NPC30749
0.6616	Remote Similarity	NPC198390
0.6615	Remote Similarity	NPC473007
0.6614	Remote Similarity	NPC99043
0.6614	Remote Similarity	NPC218594
0.6611	Remote Similarity	NPC36836
0.6611	Remote Similarity	NPC63370
0.66	Remote Similarity	NPC127178
0.66	Remote Similarity	NPC475489
0.6599	Remote Similarity	NPC230313
0.6598	Remote Similarity	NPC477998
0.6597	Remote Similarity	NPC159963
0.6595	Remote Similarity	NPC473484
0.6595	Remote Similarity	NPC475248
0.6595	Remote Similarity	NPC63047
0.6593	Remote Similarity	NPC474058
0.659	Remote Similarity	NPC475316
0.659	Remote Similarity	NPC473486
0.6584	Remote Similarity	NPC295548
0.6582	Remote Similarity	NPC114039
0.6582	Remote Similarity	NPC206109
0.6578	Remote Similarity	NPC73280
0.6575	Remote Similarity	NPC123241
0.657	Remote Similarity	NPC116178
0.6569	Remote Similarity	NPC475835
0.6569	Remote Similarity	NPC198160
0.6569	Remote Similarity	NPC472538
0.6567	Remote Similarity	NPC136573
0.6567	Remote Similarity	NPC176371
0.6567	Remote Similarity	NPC471489
0.6564	Remote Similarity	NPC473008
0.6564	Remote Similarity	NPC473298
0.6561	Remote Similarity	NPC285941
0.6561	Remote Similarity	NPC474081
0.6558	Remote Similarity	NPC473458
0.6557	Remote Similarity	NPC476231
0.6557	Remote Similarity	NPC293458
0.6552	Remote Similarity	NPC301292
0.6552	Remote Similarity	NPC313112
0.655	Remote Similarity	NPC90358
0.655	Remote Similarity	NPC107828
0.6548	Remote Similarity	NPC470485
0.6546	Remote Similarity	NPC14994
0.6538	Remote Similarity	NPC473006
0.6538	Remote Similarity	NPC471122
0.6538	Remote Similarity	NPC321166
0.6538	Remote Similarity	NPC217903
0.6537	Remote Similarity	NPC90185
0.6537	Remote Similarity	NPC205926
0.6536	Remote Similarity	NPC122106
0.6535	Remote Similarity	NPC473005
0.6535	Remote Similarity	NPC52801
0.6535	Remote Similarity	NPC288759
0.6531	Remote Similarity	NPC203628
0.6528	Remote Similarity	NPC52262
0.6526	Remote Similarity	NPC474041
0.6522	Remote Similarity	NPC313757
0.652	Remote Similarity	NPC225400
0.652	Remote Similarity	NPC246140
0.652	Remote Similarity	NPC195787
0.6515	Remote Similarity	NPC243626
0.6512	Remote Similarity	NPC476436
0.6508	Remote Similarity	NPC475607
0.6505	Remote Similarity	NPC477160
0.6503	Remote Similarity	NPC248117
0.6502	Remote Similarity	NPC41216
0.6498	Remote Similarity	NPC223242
0.6497	Remote Similarity	NPC212799
0.6497	Remote Similarity	NPC254798
0.6495	Remote Similarity	NPC116007
0.6492	Remote Similarity	NPC286994
0.6492	Remote Similarity	NPC11149
0.649	Remote Similarity	NPC470482
0.649	Remote Similarity	NPC470481
0.6489	Remote Similarity	NPC473748
0.6488	Remote Similarity	NPC470786
0.6488	Remote Similarity	NPC212123
0.6488	Remote Similarity	NPC471155
0.6486	Remote Similarity	NPC471124
0.6484	Remote Similarity	NPC104345
0.648	Remote Similarity	NPC312531
0.648	Remote Similarity	NPC5630
0.6476	Remote Similarity	NPC30570
0.6471	Remote Similarity	NPC475147
0.6467	Remote Similarity	NPC176983
0.6467	Remote Similarity	NPC282339
0.6467	Remote Similarity	NPC99632
0.6464	Remote Similarity	NPC161827
0.6462	Remote Similarity	NPC473815

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 NPC307640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	621
0.2-0.3	912
0.3-0.4	1583
0.4-0.5	2705
0.5-0.6	2187
0.6-0.7	685
0.7-0.8	82
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7389	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4430	Phase 2
0.7348	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2791	Discontinued
0.7303	Intermediate Similarity	NPD5186	Approved
0.7303	Intermediate Similarity	NPD5183	Approved
0.7222	Intermediate Similarity	NPD5997	Discontinued
0.7175	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3789	Approved
0.7059	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6457	Approved
0.7005	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5071	Phase 2
0.6833	Remote Similarity	NPD4871	Phase 2
0.6828	Remote Similarity	NPD3793	Phase 3
0.68	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7479	Phase 2
0.6782	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3277	Phase 3
0.6755	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2670	Approved
0.6736	Remote Similarity	NPD5928	Phase 1
0.6732	Remote Similarity	NPD7225	Discontinued
0.6721	Remote Similarity	NPD5823	Approved
0.672	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD8149	Discontinued
0.6707	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7487	Discontinued
0.6703	Remote Similarity	NPD8007	Approved
0.6703	Remote Similarity	NPD8008	Approved
0.6687	Remote Similarity	NPD6320	Approved
0.6686	Remote Similarity	NPD7478	Approved
0.6685	Remote Similarity	NPD5086	Approved
0.6684	Remote Similarity	NPD8281	Discontinued
0.6684	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6238	Discontinued
0.6647	Remote Similarity	NPD2820	Phase 3
0.6633	Remote Similarity	NPD6874	Approved
0.6633	Remote Similarity	NPD5610	Approved
0.6631	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6570	Approved
0.6611	Remote Similarity	NPD6571	Approved
0.66	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7244	Discontinued
0.6592	Remote Similarity	NPD6357	Discontinued
0.659	Remote Similarity	NPD2365	Approved
0.6582	Remote Similarity	NPD7570	Approved
0.6582	Remote Similarity	NPD7569	Approved
0.6576	Remote Similarity	NPD7036	Phase 3
0.6576	Remote Similarity	NPD7035	Approved
0.6573	Remote Similarity	NPD7606	Phase 3
0.6573	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5600	Discontinued
0.6552	Remote Similarity	NPD7082	Approved
0.6546	Remote Similarity	NPD4515	Suspended
0.6546	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5515	Phase 2
0.6528	Remote Similarity	NPD7654	Discontinued
0.6526	Remote Similarity	NPD8311	Discontinued
0.6514	Remote Similarity	NPD7259	Approved
0.651	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7600	Phase 2
0.65	Remote Similarity	NPD3229	Phase 2
0.6488	Remote Similarity	NPD7263	Phase 2
0.6485	Remote Similarity	NPD6321	Discontinued
0.6477	Remote Similarity	NPD7295	Approved
0.6477	Remote Similarity	NPD3301	Approved
0.6477	Remote Similarity	NPD6185	Discontinued
0.6473	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5847	Phase 1
0.6461	Remote Similarity	NPD4888	Discontinued
0.6461	Remote Similarity	NPD2335	Discontinued
0.6456	Remote Similarity	NPD4859	Phase 1
0.6455	Remote Similarity	NPD7940	Phase 3
0.6447	Remote Similarity	NPD7668	Phase 2
0.6441	Remote Similarity	NPD4041	Approved
0.6436	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD1307	Phase 2
0.6432	Remote Similarity	NPD1309	Phase 2
0.6429	Remote Similarity	NPD7291	Discontinued
0.6421	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7177	Discontinued
0.642	Remote Similarity	NPD2387	Approved
0.642	Remote Similarity	NPD2435	Approved
0.6416	Remote Similarity	NPD1626	Approved
0.6416	Remote Similarity	NPD3170	Approved
0.6404	Remote Similarity	NPD1802	Approved
0.6404	Remote Similarity	NPD1801	Approved
0.6404	Remote Similarity	NPD6758	Approved
0.6404	Remote Similarity	NPD8165	Discontinued
0.6402	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7854	Phase 2
0.64	Remote Similarity	NPD6768	Approved
0.64	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5430	Discontinued
0.6398	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7810	Phase 3
0.6386	Remote Similarity	NPD7811	Phase 3
0.6378	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5941	Approved
0.6369	Remote Similarity	NPD7528	Approved
0.6369	Remote Similarity	NPD5942	Approved
0.6368	Remote Similarity	NPD5466	Approved
0.6364	Remote Similarity	NPD7179	Phase 2
0.6359	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7775	Approved
0.6354	Remote Similarity	NPD7881	Approved
0.6354	Remote Similarity	NPD3399	Approved
0.635	Remote Similarity	NPD7669	Phase 3
0.6345	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7820	Phase 3
0.634	Remote Similarity	NPD7962	Phase 2
0.6339	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7110	Phase 1
0.6335	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7301	Phase 3
0.6328	Remote Similarity	NPD5918	Discontinued
0.6324	Remote Similarity	NPD3416	Discontinued
0.6324	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6878	Phase 2
0.6321	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6879	Phase 2
0.6316	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6644	Discontinued
0.631	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5923	Phase 1
0.6307	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD6566	Discontinued
0.6307	Remote Similarity	NPD2923	Approved
0.6305	Remote Similarity	NPD5609	Approved
0.6305	Remote Similarity	NPD5608	Approved
0.6305	Remote Similarity	NPD3297	Approved
0.6304	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD6020	Phase 2
0.6298	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8027	Approved
0.6296	Remote Similarity	NPD7795	Phase 2
0.6294	Remote Similarity	NPD6484	Approved
0.6294	Remote Similarity	NPD6483	Approved
0.6293	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6876	Approved
0.6284	Remote Similarity	NPD6875	Approved
0.6283	Remote Similarity	NPD7324	Discontinued
0.6283	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5042	Phase 1
0.6278	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6037	Discontinued
0.6271	Remote Similarity	NPD1625	Approved
0.6271	Remote Similarity	NPD5024	Approved
0.627	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.627	Remote Similarity	NPD3388	Phase 1
0.627	Remote Similarity	NPD7599	Phase 2
0.627	Remote Similarity	NPD6737	Phase 2
0.627	Remote Similarity	NPD6738	Phase 2
0.6269	Remote Similarity	NPD7256	Discontinued
0.6263	Remote Similarity	NPD8025	Phase 2
0.6263	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4607	Approved
0.6256	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5856	Discontinued
0.625	Remote Similarity	NPD5179	Approved
0.625	Remote Similarity	NPD2836	Approved
0.625	Remote Similarity	NPD7752	Approved
0.625	Remote Similarity	NPD5937	Approved
0.625	Remote Similarity	NPD8146	Phase 2
0.625	Remote Similarity	NPD5180	Approved
0.625	Remote Similarity	NPD5181	Approved
0.625	Remote Similarity	NPD7753	Approved
0.6244	Remote Similarity	NPD7476	Discontinued
0.6243	Remote Similarity	NPD3983	Phase 3
0.6243	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5582	Discontinued
0.6238	Remote Similarity	NPD3964	Approved
0.6232	Remote Similarity	NPD3298	Approved
0.6232	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6250	Discontinued
0.6231	Remote Similarity	NPD5114	Approved
0.6231	Remote Similarity	NPD5112	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