NPASS Compound

Structure

NPC300183 OpenBabel07101719152D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.0019 3.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3099 2.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9049 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9049 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6230 -3.3223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5741 -3.0133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8799 -2.6532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7820 -2.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6267 1.9830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6316 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6084 3.1183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0956 2.9252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3951 1.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2575 2.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5784 2.3341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8282 3.2082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -0.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7015 4.2001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 20 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 24 2 0 0 0 0 8 26 2 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 32 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 31 1 0 0 0 0 21 24 1 0 0 0 0 22 10 1 1 0 0 0 22 30 1 0 0 0 0 23 33 1 6 0 0 0 24 26 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 26 31 1 0 0 0 0 27 17 1 1 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 30 1 0 0 0 0 29 32 1 0 0 0 0 29 34 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.29
Volume:	503.136
LogP:	6.196
LogD:	4.658
LogS:	-5.054
# Rotatable Bonds:	3
TPSA:	61.18
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	5.304
Fsp3:	0.467
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:	-5.316
MDCK Permeability:	1.6732867152313702e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	97.96575164794922%
Volume Distribution (VD):	0.663
Pgp-substrate:	1.1228835582733154%

ADMET: Metabolism

CYP1A2-inhibitor:	0.246
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.164
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.783
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	5.555
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.299
Carcinogencity:	0.402
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC300183

Natural Product ID:	NPC300183
*Common Name:**	Cespitulactam J
IUPAC Name:	n.a.
Synonyms:	Cespitulactam J
Standard InCHIKey:	ABTDHHPHHKFQBT-USINTNLNSA-N
Standard InCHI:	InChI=1S/C30H38N2O2/c1-19-9-10-22-11-12-25-28(30(22,3)4)27(17-20(2)16-23(33)15-19)32(29(25)34)14-13-21-18-31-26-8-6-5-7-24(21)26/h5-8,16,18,22-23,27,31,33H,1,9-15,17H2,2-4H3/b20-16+/t22-,23+,27-/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C([C@@H](C/C(=C/[C@H](C1)O)/C)N(CCc1c[nH]c4ccccc14)C3=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399540
PubChem CID:	24762991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16495058]
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	Taiwanese soft coral	n.a.	PMID[18052327]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.16	ug.mL-1	PMID[575685]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	4.16	ug.mL-1	PMID[575685]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	=	4.16	ug.mL-1	PMID[575685]

☑ 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 NPC300183 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	282
0.1-0.2	1472
0.2-0.3	8670
0.3-0.4	22546
0.4-0.5	4648
0.5-0.6	2493
0.6-0.7	1819
0.7-0.8	712
0.8-0.85	33
0.85-0.9	13
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC98715
0.9202	High Similarity	NPC46225
0.9202	High Similarity	NPC225821
0.9153	High Similarity	NPC127677
0.9153	High Similarity	NPC258062
0.8964	High Similarity	NPC151976
0.8964	High Similarity	NPC87856
0.8919	High Similarity	NPC157828
0.8919	High Similarity	NPC195239
0.8918	High Similarity	NPC267965
0.8906	High Similarity	NPC271862
0.8871	High Similarity	NPC11445
0.8827	High Similarity	NPC132211
0.8731	High Similarity	NPC204491
0.8731	High Similarity	NPC203614
0.8607	High Similarity	NPC2395
0.8462	Intermediate Similarity	NPC151939
0.8415	Intermediate Similarity	NPC213468
0.839	Intermediate Similarity	NPC235885
0.839	Intermediate Similarity	NPC141428
0.8342	Intermediate Similarity	NPC94752
0.8341	Intermediate Similarity	NPC147446
0.8333	Intermediate Similarity	NPC228835
0.8333	Intermediate Similarity	NPC201700
0.8316	Intermediate Similarity	NPC47190
0.8309	Intermediate Similarity	NPC57690
0.827	Intermediate Similarity	NPC300688
0.8268	Intermediate Similarity	NPC311276
0.8241	Intermediate Similarity	NPC162860
0.8196	Intermediate Similarity	NPC131887
0.8163	Intermediate Similarity	NPC475506
0.8158	Intermediate Similarity	NPC213629
0.8146	Intermediate Similarity	NPC469762
0.8141	Intermediate Similarity	NPC54420
0.8122	Intermediate Similarity	NPC155143
0.8118	Intermediate Similarity	NPC11126
0.8105	Intermediate Similarity	NPC17059
0.809	Intermediate Similarity	NPC469785
0.8086	Intermediate Similarity	NPC267926
0.8077	Intermediate Similarity	NPC266192
0.8066	Intermediate Similarity	NPC40779
0.806	Intermediate Similarity	NPC478158
0.8021	Intermediate Similarity	NPC95783
0.8021	Intermediate Similarity	NPC215795
0.8021	Intermediate Similarity	NPC176199
0.802	Intermediate Similarity	NPC252338
0.801	Intermediate Similarity	NPC473640
0.801	Intermediate Similarity	NPC477044
0.801	Intermediate Similarity	NPC477041
0.8	Intermediate Similarity	NPC280290
0.799	Intermediate Similarity	NPC267343
0.799	Intermediate Similarity	NPC474177
0.7978	Intermediate Similarity	NPC259644
0.7978	Intermediate Similarity	NPC469786
0.7978	Intermediate Similarity	NPC469760
0.7978	Intermediate Similarity	NPC25008
0.7978	Intermediate Similarity	NPC469763
0.7978	Intermediate Similarity	NPC469765
0.7978	Intermediate Similarity	NPC73952
0.797	Intermediate Similarity	NPC107077
0.797	Intermediate Similarity	NPC100321
0.797	Intermediate Similarity	NPC477045
0.797	Intermediate Similarity	NPC223791
0.7962	Intermediate Similarity	NPC476491
0.7959	Intermediate Similarity	NPC227582
0.7951	Intermediate Similarity	NPC478157
0.7949	Intermediate Similarity	NPC133366
0.7933	Intermediate Similarity	NPC212376
0.7933	Intermediate Similarity	NPC75540
0.7933	Intermediate Similarity	NPC70922
0.7933	Intermediate Similarity	NPC211572
0.7933	Intermediate Similarity	NPC80597
0.7919	Intermediate Similarity	NPC171317
0.7914	Intermediate Similarity	NPC267885
0.7903	Intermediate Similarity	NPC34508
0.7903	Intermediate Similarity	NPC313791
0.7902	Intermediate Similarity	NPC54744
0.7892	Intermediate Similarity	NPC320968
0.788	Intermediate Similarity	NPC160105
0.788	Intermediate Similarity	NPC474561
0.788	Intermediate Similarity	NPC49954
0.7872	Intermediate Similarity	NPC64436
0.7872	Intermediate Similarity	NPC68354
0.7869	Intermediate Similarity	NPC102423
0.7865	Intermediate Similarity	NPC24678
0.7865	Intermediate Similarity	NPC315555
0.7865	Intermediate Similarity	NPC235684
0.7865	Intermediate Similarity	NPC105818
0.7861	Intermediate Similarity	NPC37423
0.7861	Intermediate Similarity	NPC149155
0.7861	Intermediate Similarity	NPC275305
0.7861	Intermediate Similarity	NPC110500
0.7861	Intermediate Similarity	NPC473376
0.7861	Intermediate Similarity	NPC477043
0.7861	Intermediate Similarity	NPC203468
0.7857	Intermediate Similarity	NPC294693
0.7854	Intermediate Similarity	NPC75634
0.785	Intermediate Similarity	NPC290529
0.785	Intermediate Similarity	NPC476874
0.7849	Intermediate Similarity	NPC6982
0.7838	Intermediate Similarity	NPC78020
0.7837	Intermediate Similarity	NPC281049
0.7835	Intermediate Similarity	NPC154339
0.7835	Intermediate Similarity	NPC206967
0.7831	Intermediate Similarity	NPC248041
0.7831	Intermediate Similarity	NPC126709
0.7831	Intermediate Similarity	NPC248462
0.783	Intermediate Similarity	NPC319232
0.783	Intermediate Similarity	NPC24370
0.7795	Intermediate Similarity	NPC117244
0.7795	Intermediate Similarity	NPC473763
0.7789	Intermediate Similarity	NPC293917
0.7784	Intermediate Similarity	NPC65215
0.7784	Intermediate Similarity	NPC321708
0.7784	Intermediate Similarity	NPC173028
0.7784	Intermediate Similarity	NPC54988
0.7778	Intermediate Similarity	NPC145885
0.7778	Intermediate Similarity	NPC84827
0.7778	Intermediate Similarity	NPC14113
0.7778	Intermediate Similarity	NPC70155
0.7761	Intermediate Similarity	NPC476073
0.7761	Intermediate Similarity	NPC260900
0.776	Intermediate Similarity	NPC131718
0.776	Intermediate Similarity	NPC165495
0.7751	Intermediate Similarity	NPC473310
0.7751	Intermediate Similarity	NPC477714
0.7749	Intermediate Similarity	NPC71037
0.7749	Intermediate Similarity	NPC233936
0.7739	Intermediate Similarity	NPC265576
0.7737	Intermediate Similarity	NPC283219
0.7737	Intermediate Similarity	NPC270009
0.7732	Intermediate Similarity	NPC204565
0.7732	Intermediate Similarity	NPC317030
0.7732	Intermediate Similarity	NPC278434
0.772	Intermediate Similarity	NPC163421
0.772	Intermediate Similarity	NPC188387
0.7717	Intermediate Similarity	NPC282231
0.7713	Intermediate Similarity	NPC314603
0.7708	Intermediate Similarity	NPC19679
0.7705	Intermediate Similarity	NPC230869
0.7703	Intermediate Similarity	NPC472285
0.7701	Intermediate Similarity	NPC194411
0.77	Intermediate Similarity	NPC74413
0.7696	Intermediate Similarity	NPC91179
0.7696	Intermediate Similarity	NPC198339
0.7688	Intermediate Similarity	NPC229332
0.7684	Intermediate Similarity	NPC111275
0.768	Intermediate Similarity	NPC474707
0.7676	Intermediate Similarity	NPC194640
0.7668	Intermediate Similarity	NPC477003
0.7663	Intermediate Similarity	NPC279918
0.7662	Intermediate Similarity	NPC470497
0.766	Intermediate Similarity	NPC470498
0.7656	Intermediate Similarity	NPC471192
0.7656	Intermediate Similarity	NPC192270
0.7653	Intermediate Similarity	NPC83111
0.765	Intermediate Similarity	NPC89987
0.7647	Intermediate Similarity	NPC154293
0.7647	Intermediate Similarity	NPC63751
0.7644	Intermediate Similarity	NPC55772
0.7644	Intermediate Similarity	NPC229348
0.764	Intermediate Similarity	NPC159856
0.764	Intermediate Similarity	NPC314372
0.7637	Intermediate Similarity	NPC470507
0.7619	Intermediate Similarity	NPC477715
0.7617	Intermediate Similarity	NPC469358
0.7615	Intermediate Similarity	NPC323752
0.7614	Intermediate Similarity	NPC243716
0.7614	Intermediate Similarity	NPC476460
0.7609	Intermediate Similarity	NPC92796
0.7609	Intermediate Similarity	NPC135141
0.7604	Intermediate Similarity	NPC477042
0.7596	Intermediate Similarity	NPC153980
0.7596	Intermediate Similarity	NPC6865
0.7592	Intermediate Similarity	NPC293472
0.7586	Intermediate Similarity	NPC193761
0.7583	Intermediate Similarity	NPC264285
0.7581	Intermediate Similarity	NPC472762
0.7562	Intermediate Similarity	NPC67288
0.7562	Intermediate Similarity	NPC470499
0.7561	Intermediate Similarity	NPC475288
0.7558	Intermediate Similarity	NPC326363
0.7558	Intermediate Similarity	NPC470730
0.7558	Intermediate Similarity	NPC477176
0.7558	Intermediate Similarity	NPC470729
0.7558	Intermediate Similarity	NPC477175
0.7554	Intermediate Similarity	NPC286427
0.7552	Intermediate Similarity	NPC472443
0.7548	Intermediate Similarity	NPC72956
0.7538	Intermediate Similarity	NPC308931
0.7538	Intermediate Similarity	NPC99939
0.7528	Intermediate Similarity	NPC190296
0.7526	Intermediate Similarity	NPC163055
0.7526	Intermediate Similarity	NPC472444
0.7526	Intermediate Similarity	NPC97525
0.7525	Intermediate Similarity	NPC138370
0.7524	Intermediate Similarity	NPC313640
0.7523	Intermediate Similarity	NPC475859
0.7523	Intermediate Similarity	NPC477177
0.7523	Intermediate Similarity	NPC474877

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 NPC300183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	518
0.2-0.3	654
0.3-0.4	1680
0.4-0.5	2650
0.5-0.6	2334
0.6-0.7	966
0.7-0.8	168
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
0.8168	Intermediate Similarity	NPD8094	Discontinued
0.8119	Intermediate Similarity	NPD8093	Discontinued
0.8085	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD7470	Discontinued
0.805	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD2144	Approved
0.7959	Intermediate Similarity	NPD6664	Approved
0.7949	Intermediate Similarity	NPD7618	Phase 3
0.7949	Intermediate Similarity	NPD7619	Phase 3
0.7937	Intermediate Similarity	NPD3038	Discontinued
0.7931	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD4076	Approved
0.7926	Intermediate Similarity	NPD4079	Approved
0.7872	Intermediate Similarity	NPD3505	Approved
0.7872	Intermediate Similarity	NPD3506	Approved
0.7861	Intermediate Similarity	NPD5065	Approved
0.7861	Intermediate Similarity	NPD482	Approved
0.7861	Intermediate Similarity	NPD5426	Phase 3
0.7857	Intermediate Similarity	NPD7944	Discontinued
0.7838	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7837	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD2509	Approved
0.7833	Intermediate Similarity	NPD2510	Approved
0.7824	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7001	Phase 3
0.7819	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD4075	Phase 2
0.7801	Intermediate Similarity	NPD2095	Phase 2
0.7801	Intermediate Similarity	NPD2092	Phase 2
0.7801	Intermediate Similarity	NPD2094	Phase 2
0.7789	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6999	Discontinued
0.7772	Intermediate Similarity	NPD8272	Phase 2
0.7772	Intermediate Similarity	NPD5901	Discontinued
0.776	Intermediate Similarity	NPD2096	Phase 2
0.776	Intermediate Similarity	NPD2091	Phase 2
0.776	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD750	Phase 2
0.7711	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD6595	Phase 3
0.768	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6176	Phase 1
0.7614	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2511	Approved
0.7561	Intermediate Similarity	NPD7957	Phase 1
0.7561	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8431	Approved
0.7549	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7603	Discontinued
0.75	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD3394	Approved
0.7488	Intermediate Similarity	NPD7665	Phase 2
0.7488	Intermediate Similarity	NPD3393	Approved
0.7488	Intermediate Similarity	NPD4600	Approved
0.7488	Intermediate Similarity	NPD484	Approved
0.7488	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7666	Phase 3
0.7488	Intermediate Similarity	NPD3389	Approved
0.7488	Intermediate Similarity	NPD4601	Approved
0.7487	Intermediate Similarity	NPD7564	Discontinued
0.7477	Intermediate Similarity	NPD7824	Approved
0.7465	Intermediate Similarity	NPD6164	Phase 2
0.7465	Intermediate Similarity	NPD6165	Phase 2
0.7462	Intermediate Similarity	NPD3961	Discontinued
0.746	Intermediate Similarity	NPD4640	Approved
0.746	Intermediate Similarity	NPD4639	Approved
0.746	Intermediate Similarity	NPD4638	Approved
0.746	Intermediate Similarity	NPD2844	Phase 3
0.7453	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6376	Discontinued
0.7387	Intermediate Similarity	NPD4499	Approved
0.7387	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7730	Approved
0.7385	Intermediate Similarity	NPD7731	Approved
0.7379	Intermediate Similarity	NPD8072	Approved
0.7377	Intermediate Similarity	NPD2172	Phase 1
0.7377	Intermediate Similarity	NPD4463	Approved
0.7377	Intermediate Similarity	NPD4462	Approved
0.7376	Intermediate Similarity	NPD7789	Approved
0.7376	Intermediate Similarity	NPD7791	Approved
0.7376	Intermediate Similarity	NPD7952	Approved
0.7376	Intermediate Similarity	NPD7953	Approved
0.7376	Intermediate Similarity	NPD7790	Approved
0.7376	Intermediate Similarity	NPD7951	Approved
0.7376	Intermediate Similarity	NPD7950	Approved
0.7373	Intermediate Similarity	NPD7271	Approved
0.7361	Intermediate Similarity	NPD6995	Phase 1
0.736	Intermediate Similarity	NPD786	Approved
0.7356	Intermediate Similarity	NPD8322	Phase 2
0.7353	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7781	Approved
0.7352	Intermediate Similarity	NPD7780	Approved
0.7347	Intermediate Similarity	NPD5596	Phase 2
0.7343	Intermediate Similarity	NPD8115	Approved
0.7343	Intermediate Similarity	NPD8114	Approved
0.734	Intermediate Similarity	NPD7948	Phase 1
0.7339	Intermediate Similarity	NPD8289	Discontinued
0.7337	Intermediate Similarity	NPD7234	Approved
0.7337	Intermediate Similarity	NPD7233	Approved
0.7337	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5897	Approved
0.7333	Intermediate Similarity	NPD5898	Approved
0.7333	Intermediate Similarity	NPD5899	Approved
0.733	Intermediate Similarity	NPD7187	Phase 2
0.733	Intermediate Similarity	NPD1325	Approved
0.733	Intermediate Similarity	NPD1326	Approved
0.7323	Intermediate Similarity	NPD6217	Discontinued
0.7322	Intermediate Similarity	NPD3100	Discontinued
0.732	Intermediate Similarity	NPD4181	Approved
0.7313	Intermediate Similarity	NPD6665	Discontinued
0.7302	Intermediate Similarity	NPD5138	Approved
0.7302	Intermediate Similarity	NPD5140	Approved
0.7302	Intermediate Similarity	NPD3323	Discontinued
0.7297	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3178	Discontinued
0.729	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7817	Phase 1
0.7278	Intermediate Similarity	NPD1592	Phase 3
0.7278	Intermediate Similarity	NPD1722	Approved
0.7277	Intermediate Similarity	NPD7970	Approved
0.7277	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5555	Phase 1
0.7268	Intermediate Similarity	NPD6248	Phase 2
0.7268	Intermediate Similarity	NPD6249	Phase 2
0.7268	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4702	Approved
0.7268	Intermediate Similarity	NPD4703	Approved
0.7264	Intermediate Similarity	NPD4852	Phase 2
0.7259	Intermediate Similarity	NPD3319	Phase 1
0.7259	Intermediate Similarity	NPD3318	Approved
0.7259	Intermediate Similarity	NPD3320	Approved
0.7251	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD8073	Approved
0.7241	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5505	Discontinued
0.7225	Intermediate Similarity	NPD7010	Phase 3
0.7216	Intermediate Similarity	NPD4128	Approved
0.7214	Intermediate Similarity	NPD6281	Approved
0.7209	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7308	Discontinued
0.7177	Intermediate Similarity	NPD6987	Phase 1
0.7177	Intermediate Similarity	NPD3947	Discontinued
0.7176	Intermediate Similarity	NPD7878	Phase 2
0.7164	Intermediate Similarity	NPD4334	Discontinued
0.7156	Intermediate Similarity	NPD2916	Discontinued
0.715	Intermediate Similarity	NPD4500	Approved
0.715	Intermediate Similarity	NPD4501	Approved
0.715	Intermediate Similarity	NPD6479	Discontinued
0.7143	Intermediate Similarity	NPD4922	Phase 2
0.7136	Intermediate Similarity	NPD6178	Phase 3
0.7129	Intermediate Similarity	NPD5487	Phase 1
0.7129	Intermediate Similarity	NPD3321	Discontinued
0.7128	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6026	Approved
0.7122	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3583	Phase 2
0.7115	Intermediate Similarity	NPD7727	Phase 2
0.7114	Intermediate Similarity	NPD4948	Discontinued
0.7113	Intermediate Similarity	NPD3609	Approved
0.7113	Intermediate Similarity	NPD3610	Approved
0.711	Intermediate Similarity	NPD6242	Discontinued
0.7108	Intermediate Similarity	NPD1038	Approved
0.7105	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD2640	Approved
0.7098	Intermediate Similarity	NPD2641	Approved
0.7098	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2380	Approved
0.7092	Intermediate Similarity	NPD2382	Approved
0.7092	Intermediate Similarity	NPD2381	Approved
0.7092	Intermediate Similarity	NPD5100	Phase 3
0.7091	Intermediate Similarity	NPD6850	Phase 2
0.7091	Intermediate Similarity	NPD6849	Phase 2
0.7071	Intermediate Similarity	NPD5473	Discontinued
0.707	Intermediate Similarity	NPD3794	Approved
0.707	Intermediate Similarity	NPD3795	Approved
0.7059	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3404	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