NPASS Compound

Structure

NPC65215 OpenBabel07101718272D 32 34 0 0 1 0 0 0 0 0999 V2000 -4.9939 -3.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7618 -6.1408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2618 -7.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5692 -2.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1044 -0.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7618 -2.6767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1278 -4.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 -5.2748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2618 -5.2748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 -3.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 -3.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7618 -4.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3275 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7322 -0.4601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 1.2157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7618 -6.1408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3613 -1.5715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 -0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 0.2157 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3958 -3.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 -2.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 -1.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -2.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4102 -1.2625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4102 -0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 -3.5427 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1389 -1.3736 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 0.0000 -1.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2023 1.7157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3613 -0.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 7 30 1 0 0 0 0 8 27 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 17 2 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 28 1 0 0 0 0 16 31 1 0 0 0 0 19 23 1 0 0 0 0 20 16 1 1 0 0 0 20 29 1 0 0 0 0 21 24 2 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 24 28 1 0 0 0 0 25 18 1 6 0 0 0 25 26 1 0 0 0 0 25 30 1 0 0 0 0 26 29 2 3 0 0 0 26 32 1 0 0 0 0 27 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	437.3
Volume:	481.994
LogP:	5.515
LogD:	4.082
LogS:	-4.148
# Rotatable Bonds:	7
TPSA:	68.36
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	4.939
Fsp3:	0.519
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895
MDCK Permeability:	9.7840047601494e-06
Pgp-inhibitor:	0.464
Pgp-substrate:	0.865
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.772
Plasma Protein Binding (PPB):	91.00194549560547%
Volume Distribution (VD):	1.255
Pgp-substrate:	6.978846549987793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.411
CYP1A2-substrate:	0.455
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.583
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.632
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.614

ADMET: Excretion

Clearance (CL):	9.187
Half-life (T1/2):	0.146

ADMET: Toxicity

hERG Blockers:	0.628
Human Hepatotoxicity (H-HT):	0.872
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.386
Carcinogencity:	0.34
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC65215

Natural Product ID:	NPC65215
*Common Name:**	KISDGNGREAJPQR-QOAWAWRESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KISDGNGREAJPQR-QOAWAWRESA-N
Standard InCHI:	InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27+/m0/s1
SMILES:	C=C[C@](C)(CCC=C(C)C)c1ccc2c3c(C[C@@H](CO)N=C([C@H](C(C)C)N2C)O)c[nH]c13
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472644
PubChem CID:	13749857
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002309] Alpha amino acid amides

*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
NPO32594	streptoverticillium blastmyceticum	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8201310]

☑ 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	4

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	1.05	cpm	PMID[568157]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	1.57	cpm	PMID[568157]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	4.59	cpm	PMID[568157]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	8.36	cpm	PMID[568157]
NPT2	Others	Unspecified		IC50	=	870963589.96	nM	PMID[568157]

☑ 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 NPC65215 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	380
0.1-0.2	2663
0.2-0.3	20246
0.3-0.4	12207
0.4-0.5	3134
0.5-0.6	2206
0.6-0.7	1358
0.7-0.8	428
0.8-0.85	48
0.85-0.9	17
0.9-0.95	1
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173028
0.994	High Similarity	NPC204565
0.988	High Similarity	NPC474707
0.9821	High Similarity	NPC317030
0.9766	High Similarity	NPC474177
0.9709	High Similarity	NPC133366
0.9524	High Similarity	NPC233936
0.9486	High Similarity	NPC229332
0.8871	High Similarity	NPC314957
0.8706	High Similarity	NPC160105
0.8655	High Similarity	NPC201700
0.8596	High Similarity	NPC474561
0.8596	High Similarity	NPC49954
0.8588	High Similarity	NPC194640
0.8571	High Similarity	NPC469762
0.8512	High Similarity	NPC469785
0.8506	High Similarity	NPC314603
0.8488	Intermediate Similarity	NPC54988
0.843	Intermediate Similarity	NPC470508
0.8421	Intermediate Similarity	NPC282231
0.8393	Intermediate Similarity	NPC469786
0.8393	Intermediate Similarity	NPC469763
0.8393	Intermediate Similarity	NPC469760
0.8393	Intermediate Similarity	NPC469765
0.8393	Intermediate Similarity	NPC25008
0.8393	Intermediate Similarity	NPC259644
0.8393	Intermediate Similarity	NPC73952
0.8372	Intermediate Similarity	NPC311276
0.8363	Intermediate Similarity	NPC279918
0.8343	Intermediate Similarity	NPC80597
0.8343	Intermediate Similarity	NPC70922
0.8343	Intermediate Similarity	NPC211572
0.8343	Intermediate Similarity	NPC212376
0.8343	Intermediate Similarity	NPC75540
0.8333	Intermediate Similarity	NPC63751
0.8314	Intermediate Similarity	NPC16667
0.8304	Intermediate Similarity	NPC67056
0.8268	Intermediate Similarity	NPC300688
0.8266	Intermediate Similarity	NPC40779
0.8258	Intermediate Similarity	NPC151939
0.8207	Intermediate Similarity	NPC95783
0.8198	Intermediate Similarity	NPC230869
0.8182	Intermediate Similarity	NPC280548
0.8177	Intermediate Similarity	NPC163055
0.8156	Intermediate Similarity	NPC68354
0.8152	Intermediate Similarity	NPC213629
0.814	Intermediate Similarity	NPC129721
0.8129	Intermediate Similarity	NPC207726
0.8095	Intermediate Similarity	NPC473640
0.809	Intermediate Similarity	NPC34508
0.8081	Intermediate Similarity	NPC285469
0.8056	Intermediate Similarity	NPC248454
0.8056	Intermediate Similarity	NPC59269
0.8053	Intermediate Similarity	NPC100321
0.8045	Intermediate Similarity	NPC37423
0.8045	Intermediate Similarity	NPC275305
0.8036	Intermediate Similarity	NPC314372
0.8033	Intermediate Similarity	NPC165495
0.8011	Intermediate Similarity	NPC248041
0.8011	Intermediate Similarity	NPC213468
0.8011	Intermediate Similarity	NPC126709
0.8	Intermediate Similarity	NPC267885
0.7969	Intermediate Similarity	NPC475506
0.7956	Intermediate Similarity	NPC145885
0.7956	Intermediate Similarity	NPC14113
0.7956	Intermediate Similarity	NPC84827
0.7953	Intermediate Similarity	NPC105818
0.7953	Intermediate Similarity	NPC24678
0.7946	Intermediate Similarity	NPC94752
0.7944	Intermediate Similarity	NPC472586
0.7944	Intermediate Similarity	NPC149155
0.7944	Intermediate Similarity	NPC189812
0.7944	Intermediate Similarity	NPC110500
0.7944	Intermediate Similarity	NPC203468
0.7944	Intermediate Similarity	NPC329688
0.7927	Intermediate Similarity	NPC155143
0.7917	Intermediate Similarity	NPC190296
0.7912	Intermediate Similarity	NPC283219
0.7912	Intermediate Similarity	NPC176199
0.7912	Intermediate Similarity	NPC270009
0.7912	Intermediate Similarity	NPC215795
0.788	Intermediate Similarity	NPC19679
0.7877	Intermediate Similarity	NPC194411
0.7853	Intermediate Similarity	NPC102423
0.7849	Intermediate Similarity	NPC235684
0.7833	Intermediate Similarity	NPC158129
0.7826	Intermediate Similarity	NPC192270
0.7821	Intermediate Similarity	NPC78020
0.7816	Intermediate Similarity	NPC38736
0.7814	Intermediate Similarity	NPC472443
0.7812	Intermediate Similarity	NPC265576
0.7812	Intermediate Similarity	NPC171317
0.7798	Intermediate Similarity	NPC469780
0.7798	Intermediate Similarity	NPC469768
0.7798	Intermediate Similarity	NPC469761
0.7798	Intermediate Similarity	NPC469784
0.7798	Intermediate Similarity	NPC469767
0.7798	Intermediate Similarity	NPC469783
0.7798	Intermediate Similarity	NPC469779
0.7796	Intermediate Similarity	NPC15102
0.7796	Intermediate Similarity	NPC163421
0.7796	Intermediate Similarity	NPC188387
0.779	Intermediate Similarity	NPC313791
0.779	Intermediate Similarity	NPC472123
0.7784	Intermediate Similarity	NPC472444
0.7784	Intermediate Similarity	NPC300183
0.7772	Intermediate Similarity	NPC293917
0.7751	Intermediate Similarity	NPC469766
0.7742	Intermediate Similarity	NPC228835
0.774	Intermediate Similarity	NPC131718
0.7738	Intermediate Similarity	NPC73767
0.7738	Intermediate Similarity	NPC110126
0.773	Intermediate Similarity	NPC71037
0.7722	Intermediate Similarity	NPC317430
0.7719	Intermediate Similarity	NPC159856
0.7714	Intermediate Similarity	NPC470507
0.7708	Intermediate Similarity	NPC11445
0.7688	Intermediate Similarity	NPC223791
0.7688	Intermediate Similarity	NPC187951
0.7688	Intermediate Similarity	NPC107077
0.7677	Intermediate Similarity	NPC54420
0.7672	Intermediate Similarity	NPC321708
0.7663	Intermediate Similarity	NPC293472
0.7663	Intermediate Similarity	NPC64436
0.7656	Intermediate Similarity	NPC195239
0.7656	Intermediate Similarity	NPC157828
0.7653	Intermediate Similarity	NPC476874
0.7641	Intermediate Similarity	NPC470497
0.7637	Intermediate Similarity	NPC470498
0.763	Intermediate Similarity	NPC471957
0.7626	Intermediate Similarity	NPC475288
0.7624	Intermediate Similarity	NPC475602
0.7622	Intermediate Similarity	NPC248462
0.7619	Intermediate Similarity	NPC17059
0.7619	Intermediate Similarity	NPC84911
0.7619	Intermediate Similarity	NPC105127
0.7614	Intermediate Similarity	NPC98715
0.7612	Intermediate Similarity	NPC320968
0.7609	Intermediate Similarity	NPC134586
0.7609	Intermediate Similarity	NPC288785
0.76	Intermediate Similarity	NPC271862
0.76	Intermediate Similarity	NPC162860
0.7594	Intermediate Similarity	NPC139291
0.7594	Intermediate Similarity	NPC48938
0.7594	Intermediate Similarity	NPC469358
0.7594	Intermediate Similarity	NPC472108
0.7592	Intermediate Similarity	NPC243716
0.7588	Intermediate Similarity	NPC473362
0.7588	Intermediate Similarity	NPC166492
0.7586	Intermediate Similarity	NPC124005
0.7586	Intermediate Similarity	NPC37548
0.7584	Intermediate Similarity	NPC206819
0.7584	Intermediate Similarity	NPC41257
0.7584	Intermediate Similarity	NPC56765
0.7584	Intermediate Similarity	NPC318065
0.7579	Intermediate Similarity	NPC46413
0.7577	Intermediate Similarity	NPC262898
0.7576	Intermediate Similarity	NPC473376
0.7574	Intermediate Similarity	NPC75634
0.7572	Intermediate Similarity	NPC129042
0.7568	Intermediate Similarity	NPC211997
0.7566	Intermediate Similarity	NPC171171
0.7566	Intermediate Similarity	NPC315555
0.7563	Intermediate Similarity	NPC193761
0.7561	Intermediate Similarity	NPC477714
0.756	Intermediate Similarity	NPC29886
0.756	Intermediate Similarity	NPC96102
0.756	Intermediate Similarity	NPC261195
0.7556	Intermediate Similarity	NPC90723
0.7556	Intermediate Similarity	NPC472587
0.7552	Intermediate Similarity	NPC477167
0.7552	Intermediate Similarity	NPC473342
0.755	Intermediate Similarity	NPC127677
0.755	Intermediate Similarity	NPC258062
0.7538	Intermediate Similarity	NPC470499
0.7528	Intermediate Similarity	NPC286427
0.7527	Intermediate Similarity	NPC55772
0.7527	Intermediate Similarity	NPC11126
0.7527	Intermediate Similarity	NPC154293
0.7527	Intermediate Similarity	NPC133261
0.7526	Intermediate Similarity	NPC179701
0.7513	Intermediate Similarity	NPC280290
0.7513	Intermediate Similarity	NPC314002
0.7513	Intermediate Similarity	NPC62510
0.7512	Intermediate Similarity	NPC478158
0.75	Intermediate Similarity	NPC473763
0.75	Intermediate Similarity	NPC323927
0.75	Intermediate Similarity	NPC225821
0.75	Intermediate Similarity	NPC46225
0.75	Intermediate Similarity	NPC472109
0.75	Intermediate Similarity	NPC117244
0.75	Intermediate Similarity	NPC472110
0.7486	Intermediate Similarity	NPC135141
0.7486	Intermediate Similarity	NPC92796
0.7473	Intermediate Similarity	NPC49217
0.7473	Intermediate Similarity	NPC111275
0.7472	Intermediate Similarity	NPC184476
0.746	Intermediate Similarity	NPC204717
0.7459	Intermediate Similarity	NPC78375
0.7459	Intermediate Similarity	NPC469813

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 NPC65215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	548
0.2-0.3	1065
0.3-0.4	1665
0.4-0.5	2730
0.5-0.6	2062
0.6-0.7	748
0.7-0.8	124
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8497	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD2144	Approved
0.8427	Intermediate Similarity	NPD3038	Discontinued
0.8389	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD6595	Phase 3
0.8212	Intermediate Similarity	NPD4079	Approved
0.8212	Intermediate Similarity	NPD4076	Approved
0.8156	Intermediate Similarity	NPD3505	Approved
0.8156	Intermediate Similarity	NPD3506	Approved
0.8156	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD8431	Approved
0.7957	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD2172	Phase 1
0.7944	Intermediate Similarity	NPD482	Approved
0.7921	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8386	Phase 2
0.7901	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3100	Discontinued
0.788	Intermediate Similarity	NPD2094	Phase 2
0.788	Intermediate Similarity	NPD2092	Phase 2
0.788	Intermediate Similarity	NPD2095	Phase 2
0.788	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD8272	Phase 2
0.7845	Intermediate Similarity	NPD5065	Approved
0.7838	Intermediate Similarity	NPD2096	Phase 2
0.7838	Intermediate Similarity	NPD2091	Phase 2
0.7821	Intermediate Similarity	NPD4638	Approved
0.7821	Intermediate Similarity	NPD4640	Approved
0.7821	Intermediate Similarity	NPD4639	Approved
0.7802	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD750	Phase 2
0.7778	Intermediate Similarity	NPD1325	Approved
0.7778	Intermediate Similarity	NPD1326	Approved
0.7772	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD786	Approved
0.7644	Intermediate Similarity	NPD3404	Approved
0.764	Intermediate Similarity	NPD1403	Approved
0.764	Intermediate Similarity	NPD1404	Approved
0.7626	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7957	Phase 1
0.7624	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2640	Approved
0.7624	Intermediate Similarity	NPD5021	Discontinued
0.7624	Intermediate Similarity	NPD2641	Approved
0.7619	Intermediate Similarity	NPD3961	Discontinued
0.7619	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8072	Approved
0.7611	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2639	Approved
0.7569	Intermediate Similarity	NPD2642	Approved
0.756	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1722	Approved
0.7529	Intermediate Similarity	NPD4703	Approved
0.7529	Intermediate Similarity	NPD4702	Approved
0.7525	Intermediate Similarity	NPD7470	Discontinued
0.7514	Intermediate Similarity	NPD4075	Phase 2
0.75	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD3330	Phase 1
0.7487	Intermediate Similarity	NPD7948	Phase 1
0.7475	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4181	Approved
0.7459	Intermediate Similarity	NPD4128	Approved
0.7459	Intermediate Similarity	NPD3323	Discontinued
0.745	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3117	Approved
0.7446	Intermediate Similarity	NPD3116	Approved
0.74	Intermediate Similarity	NPD5901	Discontinued
0.7399	Intermediate Similarity	NPD3717	Discontinued
0.7394	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD8073	Approved
0.7385	Intermediate Similarity	NPD7619	Phase 3
0.7385	Intermediate Similarity	NPD7618	Phase 3
0.7385	Intermediate Similarity	NPD7944	Discontinued
0.738	Intermediate Similarity	NPD8123	Approved
0.738	Intermediate Similarity	NPD8122	Approved
0.736	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1038	Approved
0.733	Intermediate Similarity	NPD4547	Phase 3
0.733	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5426	Phase 3
0.7304	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6281	Approved
0.7268	Intermediate Similarity	NPD4499	Approved
0.7263	Intermediate Similarity	NPD2837	Discontinued
0.7259	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3610	Approved
0.7258	Intermediate Similarity	NPD3609	Approved
0.7255	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4463	Approved
0.7247	Intermediate Similarity	NPD4462	Approved
0.7243	Intermediate Similarity	NPD5862	Discovery
0.7243	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5100	Phase 3
0.7233	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5106	Approved
0.7225	Intermediate Similarity	NPD5105	Approved
0.7222	Intermediate Similarity	NPD6664	Approved
0.7188	Intermediate Similarity	NPD4957	Phase 2
0.7182	Intermediate Similarity	NPD2580	Discontinued
0.7178	Intermediate Similarity	NPD4886	Phase 2
0.7164	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD802	Phase 2
0.715	Intermediate Similarity	NPD8093	Discontinued
0.715	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5555	Phase 1
0.7143	Intermediate Similarity	NPD2380	Approved
0.7143	Intermediate Similarity	NPD2382	Approved
0.7143	Intermediate Similarity	NPD2381	Approved
0.7143	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7824	Approved
0.7128	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4998	Phase 3
0.7121	Intermediate Similarity	NPD4999	Phase 3
0.7115	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4601	Approved
0.7114	Intermediate Similarity	NPD4600	Approved
0.7114	Intermediate Similarity	NPD484	Approved
0.7103	Intermediate Similarity	NPD7271	Approved
0.7095	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8129	Discovery
0.7079	Intermediate Similarity	NPD1683	Approved
0.7073	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1392	Approved
0.7071	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3082	Discontinued
0.7062	Intermediate Similarity	NPD5254	Discontinued
0.7047	Intermediate Similarity	NPD5596	Phase 2
0.7037	Intermediate Similarity	NPD7731	Approved
0.7037	Intermediate Similarity	NPD7730	Approved
0.7033	Intermediate Similarity	NPD8094	Discontinued
0.7027	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8026	Phase 1
0.7026	Intermediate Similarity	NPD706	Phase 1
0.702	Intermediate Similarity	NPD4615	Phase 2
0.7011	Intermediate Similarity	NPD5255	Approved
0.7006	Intermediate Similarity	NPD2006	Phase 2
0.7006	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2430	Phase 2
0.7	Intermediate Similarity	NPD3654	Approved
0.6995	Remote Similarity	NPD6026	Approved
0.699	Remote Similarity	NPD8020	Approved
0.699	Remote Similarity	NPD8021	Approved
0.6989	Remote Similarity	NPD5138	Approved
0.6989	Remote Similarity	NPD5140	Approved
0.6989	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5612	Discontinued
0.6949	Remote Similarity	NPD1592	Phase 3
0.6939	Remote Similarity	NPD6217	Discontinued
0.6938	Remote Similarity	NPD5067	Phase 2
0.6938	Remote Similarity	NPD5066	Phase 2
0.6935	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5315	Discontinued
0.6934	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7423	Phase 2
0.6927	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5995	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7970	Approved
0.6915	Remote Similarity	NPD7935	Phase 2
0.6912	Remote Similarity	NPD4511	Phase 1
0.6912	Remote Similarity	NPD7711	Discontinued
0.6911	Remote Similarity	NPD2928	Phase 2
0.6908	Remote Similarity	NPD8322	Phase 2
0.6907	Remote Similarity	NPD8408	Discontinued
0.6907	Remote Similarity	NPD1707	Approved
0.6907	Remote Similarity	NPD1708	Approved
0.6904	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD2383	Phase 1
0.6904	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3115	Approved
0.6902	Remote Similarity	NPD3113	Approved
0.6902	Remote Similarity	NPD3114	Approved
0.6902	Remote Similarity	NPD3112	Approved
0.6893	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6987	Phase 1
0.689	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3013	Phase 3
0.6884	Remote Similarity	NPD5913	Phase 3
0.6884	Remote Similarity	NPD5082	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5081	Phase 1
0.6884	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2118	Approved
0.6882	Remote Similarity	NPD2119	Approved
0.6878	Remote Similarity	NPD7790	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