NPASS Compound

Structure

NPC24678 OpenBabel07101719252D 27 28 0 0 0 0 0 0 0 0999 V2000 3.1388 11.5753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7713 7.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8760 7.1165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4478 10.6243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7787 9.8811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0877 8.9301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4186 8.1869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7276 7.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0585 6.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4112 5.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 5.4223 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 1.0803 6.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5669 6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 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 0.0511 4.2633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 11 1 0 0 0 0 9 10 2 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 0 0 0 0 12 22 2 0 0 0 0 13 23 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 26 1 0 0 0 0 24 25 2 3 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.27
Volume:	418.876
LogP:	5.58
LogD:	4.402
LogS:	-3.739
# Rotatable Bonds:	12
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	2.622
Fsp3:	0.458
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:	-5.005
MDCK Permeability:	1.2784050340997055e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.801
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	97.24478912353516%
Volume Distribution (VD):	2.092
Pgp-substrate:	1.215741515159607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.726
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.682
CYP2C9-inhibitor:	0.887
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	5.261
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.573
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.972
Carcinogencity:	0.052
Eye Corrosion:	0.005
Eye Irritation:	0.249
Respiratory Toxicity:	0.484

Download Data

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

Natural Product: NPC24678

Natural Product ID:	NPC24678
*Common Name:**	Granulatamide B
IUPAC Name:	(2Z,4E)-N-[2-(1H-indol-3-yl)ethyl]-3,5-dimethyldodeca-2,4-dienamide
Synonyms:
Standard InCHIKey:	FYPDAIJQUOZGTQ-YZXPOQMXSA-N
Standard InCHI:	InChI=1S/C24H34N2O/c1-4-5-6-7-8-11-19(2)16-20(3)17-24(27)25-15-14-21-18-26-23-13-10-9-12-22(21)23/h9-10,12-13,16-18,26H,4-8,11,14-15H2,1-3H3,(H,25,27)/b19-16+,20-17-
SMILES:	CCCCCCC/C(=C/C(=CC(=NCCc1c[nH]c2c1cccc2)O)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526839
PubChem CID:	11559671
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO33039	eunicella granulata	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643049]

☑ 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
GI50	14

Activity Type	# Activity
Cell Line	12
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	7700.0	nM	PMID[519969]
NPT858	Cell Line	LNCaP	Homo sapiens	GI50	=	3500.0	nM	PMID[519969]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	10600.0	nM	PMID[519969]
NPT134	Cell Line	SK-BR-3	Homo sapiens	GI50	=	6000.0	nM	PMID[519969]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	8900.0	nM	PMID[519969]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	4300.0	nM	PMID[519969]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	=	6500.0	nM	PMID[519969]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	13800.0	nM	PMID[519969]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	8600.0	nM	PMID[519969]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	10000.0	nM	PMID[519969]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	9700.0	nM	PMID[519969]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	9000.0	nM	PMID[519969]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	8200.0	nM	PMID[519969]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	6700.0	nM	PMID[519969]

☑ 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 NPC24678 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	546
0.1-0.2	6020
0.2-0.3	19417
0.3-0.4	10085
0.4-0.5	2768
0.5-0.6	1872
0.6-0.7	1209
0.7-0.8	607
0.8-0.85	107
0.85-0.9	28
0.9-0.95	33
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC105818
0.9714	High Similarity	NPC159856
0.9574	High Similarity	NPC314372
0.9571	High Similarity	NPC190296
0.9448	High Similarity	NPC73952
0.9448	High Similarity	NPC469786
0.9448	High Similarity	NPC469765
0.9448	High Similarity	NPC259644
0.9448	High Similarity	NPC469763
0.9448	High Similarity	NPC469760
0.9448	High Similarity	NPC25008
0.9429	High Similarity	NPC469768
0.9429	High Similarity	NPC469784
0.9429	High Similarity	NPC469767
0.9429	High Similarity	NPC469779
0.9429	High Similarity	NPC469783
0.9429	High Similarity	NPC469761
0.9429	High Similarity	NPC469780
0.9384	High Similarity	NPC70922
0.9384	High Similarity	NPC75540
0.9384	High Similarity	NPC80597
0.9384	High Similarity	NPC211572
0.9384	High Similarity	NPC212376
0.9362	High Similarity	NPC469766
0.9324	High Similarity	NPC135141
0.9324	High Similarity	NPC92796
0.922	High Similarity	NPC73767
0.9214	High Similarity	NPC84911
0.9189	High Similarity	NPC469785
0.9172	High Similarity	NPC471957
0.9143	High Similarity	NPC96102
0.9143	High Similarity	NPC261195
0.9143	High Similarity	NPC29886
0.9128	High Similarity	NPC469762
0.9085	High Similarity	NPC110126
0.9078	High Similarity	NPC105127
0.9013	High Similarity	NPC311276
0.9007	High Similarity	NPC131718
0.8896	High Similarity	NPC160105
0.8896	High Similarity	NPC49217
0.8889	High Similarity	NPC40779
0.8889	High Similarity	NPC279081
0.8859	High Similarity	NPC216713
0.8857	High Similarity	NPC82295
0.88	High Similarity	NPC200214
0.8792	High Similarity	NPC53947
0.8774	High Similarity	NPC474561
0.8774	High Similarity	NPC49954
0.8766	High Similarity	NPC102423
0.8759	High Similarity	NPC230002
0.8726	High Similarity	NPC470498
0.8725	High Similarity	NPC37548
0.8718	High Similarity	NPC201700
0.8716	High Similarity	NPC288838
0.8707	High Similarity	NPC242556
0.8701	High Similarity	NPC282231
0.8688	High Similarity	NPC176199
0.8688	High Similarity	NPC215795
0.8671	High Similarity	NPC314603
0.8671	High Similarity	NPC313791
0.8662	High Similarity	NPC194411
0.8636	High Similarity	NPC279918
0.86	High Similarity	NPC321911
0.8599	High Similarity	NPC63751
0.8591	High Similarity	NPC143872
0.8571	High Similarity	NPC230869
0.8533	High Similarity	NPC201380
0.8533	High Similarity	NPC179787
0.8533	High Similarity	NPC469811
0.8526	High Similarity	NPC194640
0.8506	High Similarity	NPC286427
0.85	High Similarity	NPC37423
0.85	High Similarity	NPC275305
0.8497	Intermediate Similarity	NPC38736
0.8497	Intermediate Similarity	NPC470507
0.8487	Intermediate Similarity	NPC470823
0.8477	Intermediate Similarity	NPC187951
0.8477	Intermediate Similarity	NPC124005
0.8467	Intermediate Similarity	NPC63545
0.8452	Intermediate Similarity	NPC318065
0.8452	Intermediate Similarity	NPC56765
0.8452	Intermediate Similarity	NPC206819
0.8452	Intermediate Similarity	NPC41257
0.8431	Intermediate Similarity	NPC325903
0.8431	Intermediate Similarity	NPC141926
0.8425	Intermediate Similarity	NPC150259
0.8424	Intermediate Similarity	NPC280290
0.8418	Intermediate Similarity	NPC54988
0.8395	Intermediate Similarity	NPC68354
0.8395	Intermediate Similarity	NPC248454
0.8392	Intermediate Similarity	NPC22079
0.8387	Intermediate Similarity	NPC216643
0.8377	Intermediate Similarity	NPC34844
0.8366	Intermediate Similarity	NPC470233
0.8356	Intermediate Similarity	NPC325252
0.8356	Intermediate Similarity	NPC218268
0.8344	Intermediate Similarity	NPC129042
0.8323	Intermediate Similarity	NPC184476
0.8293	Intermediate Similarity	NPC300688
0.8291	Intermediate Similarity	NPC90723
0.8288	Intermediate Similarity	NPC198988
0.8282	Intermediate Similarity	NPC151939
0.8282	Intermediate Similarity	NPC59269
0.8269	Intermediate Similarity	NPC236711
0.8263	Intermediate Similarity	NPC171171
0.8258	Intermediate Similarity	NPC471458
0.8255	Intermediate Similarity	NPC2949
0.8255	Intermediate Similarity	NPC59084
0.8253	Intermediate Similarity	NPC204717
0.825	Intermediate Similarity	NPC78020
0.8242	Intermediate Similarity	NPC233936
0.8232	Intermediate Similarity	NPC213468
0.8232	Intermediate Similarity	NPC11126
0.8228	Intermediate Similarity	NPC470203
0.8221	Intermediate Similarity	NPC267885
0.8214	Intermediate Similarity	NPC41174
0.8207	Intermediate Similarity	NPC475450
0.8204	Intermediate Similarity	NPC314002
0.82	Intermediate Similarity	NPC473868
0.82	Intermediate Similarity	NPC63157
0.8193	Intermediate Similarity	NPC220765
0.8193	Intermediate Similarity	NPC163055
0.8165	Intermediate Similarity	NPC470204
0.8165	Intermediate Similarity	NPC215584
0.8165	Intermediate Similarity	NPC44773
0.816	Intermediate Similarity	NPC110500
0.816	Intermediate Similarity	NPC149155
0.816	Intermediate Similarity	NPC203468
0.8158	Intermediate Similarity	NPC470440
0.8155	Intermediate Similarity	NPC94752
0.8153	Intermediate Similarity	NPC299594
0.8144	Intermediate Similarity	NPC228835
0.8141	Intermediate Similarity	NPC477815
0.8121	Intermediate Similarity	NPC126709
0.8121	Intermediate Similarity	NPC248041
0.8112	Intermediate Similarity	NPC250361
0.8105	Intermediate Similarity	NPC316069
0.8089	Intermediate Similarity	NPC285469
0.8089	Intermediate Similarity	NPC141353
0.8084	Intermediate Similarity	NPC48938
0.8082	Intermediate Similarity	NPC256893
0.8072	Intermediate Similarity	NPC16659
0.8069	Intermediate Similarity	NPC473587
0.8067	Intermediate Similarity	NPC88097
0.8063	Intermediate Similarity	NPC317105
0.8063	Intermediate Similarity	NPC472587
0.8061	Intermediate Similarity	NPC145885
0.8061	Intermediate Similarity	NPC14113
0.8061	Intermediate Similarity	NPC84827
0.8059	Intermediate Similarity	NPC213629
0.8054	Intermediate Similarity	NPC314102
0.8054	Intermediate Similarity	NPC125746
0.8054	Intermediate Similarity	NPC251722
0.8052	Intermediate Similarity	NPC470111
0.805	Intermediate Similarity	NPC473320
0.805	Intermediate Similarity	NPC122141
0.8047	Intermediate Similarity	NPC474707
0.8047	Intermediate Similarity	NPC235684
0.8039	Intermediate Similarity	NPC285731
0.8038	Intermediate Similarity	NPC129721
0.8035	Intermediate Similarity	NPC133366
0.8023	Intermediate Similarity	NPC99666
0.8023	Intermediate Similarity	NPC304187
0.8023	Intermediate Similarity	NPC477166
0.8014	Intermediate Similarity	NPC475428
0.8013	Intermediate Similarity	NPC115611
0.8012	Intermediate Similarity	NPC233050
0.8012	Intermediate Similarity	NPC283219
0.8012	Intermediate Similarity	NPC276540
0.8012	Intermediate Similarity	NPC265710
0.8012	Intermediate Similarity	NPC42372
0.8	Intermediate Similarity	NPC317030
0.8	Intermediate Similarity	NPC473762
0.8	Intermediate Similarity	NPC46580
0.8	Intermediate Similarity	NPC2272
0.7988	Intermediate Similarity	NPC15102
0.7977	Intermediate Similarity	NPC474177
0.7963	Intermediate Similarity	NPC109447
0.7959	Intermediate Similarity	NPC179365
0.7953	Intermediate Similarity	NPC173028
0.7953	Intermediate Similarity	NPC65215
0.7952	Intermediate Similarity	NPC284775
0.7952	Intermediate Similarity	NPC111275
0.7952	Intermediate Similarity	NPC473380
0.7952	Intermediate Similarity	NPC96890
0.7952	Intermediate Similarity	NPC240088
0.7952	Intermediate Similarity	NPC184964
0.795	Intermediate Similarity	NPC271734
0.795	Intermediate Similarity	NPC149265
0.7939	Intermediate Similarity	NPC293216
0.7935	Intermediate Similarity	NPC21605
0.7927	Intermediate Similarity	NPC6982
0.7922	Intermediate Similarity	NPC204141
0.7919	Intermediate Similarity	NPC324149
0.7919	Intermediate Similarity	NPC47190
0.7917	Intermediate Similarity	NPC243381
0.7917	Intermediate Similarity	NPC275292
0.7917	Intermediate Similarity	NPC71037
0.7907	Intermediate Similarity	NPC95783
0.7905	Intermediate Similarity	NPC473930

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 NPC24678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	675
0.2-0.3	971
0.3-0.4	1608
0.4-0.5	2580
0.5-0.6	1883
0.6-0.7	884
0.7-0.8	240
0.8-0.85	22
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.922	High Similarity	NPD786	Approved
0.9143	High Similarity	NPD198	Clinical (unspecified phase)
0.8961	High Similarity	NPD5069	Clinical (unspecified phase)
0.8958	High Similarity	NPD1722	Approved
0.8919	High Similarity	NPD4462	Approved
0.8919	High Similarity	NPD4463	Approved
0.8851	High Similarity	NPD3100	Discontinued
0.8792	High Similarity	NPD2172	Phase 1
0.8734	High Similarity	NPD5065	Approved
0.8725	High Similarity	NPD4374	Clinical (unspecified phase)
0.8662	High Similarity	NPD4184	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD2837	Discontinued
0.8397	Intermediate Similarity	NPD1403	Approved
0.8397	Intermediate Similarity	NPD1404	Approved
0.8395	Intermediate Similarity	NPD2144	Approved
0.8395	Intermediate Similarity	NPD3506	Approved
0.8395	Intermediate Similarity	NPD3505	Approved
0.8385	Intermediate Similarity	NPD4128	Approved
0.8344	Intermediate Similarity	NPD4076	Approved
0.8344	Intermediate Similarity	NPD4079	Approved
0.8302	Intermediate Similarity	NPD2642	Approved
0.8302	Intermediate Similarity	NPD2639	Approved
0.8293	Intermediate Similarity	NPD6595	Phase 3
0.8291	Intermediate Similarity	NPD3323	Discontinued
0.8282	Intermediate Similarity	NPD4181	Approved
0.8282	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD2640	Approved
0.825	Intermediate Similarity	NPD2641	Approved
0.8242	Intermediate Similarity	NPD3038	Discontinued
0.8221	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4075	Phase 2
0.8193	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD482	Approved
0.8107	Intermediate Similarity	NPD8431	Approved
0.8095	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD5254	Discontinued
0.8086	Intermediate Similarity	NPD1326	Approved
0.8086	Intermediate Similarity	NPD1325	Approved
0.8084	Intermediate Similarity	NPD2092	Phase 2
0.8084	Intermediate Similarity	NPD2095	Phase 2
0.8084	Intermediate Similarity	NPD2094	Phase 2
0.8079	Intermediate Similarity	NPD1592	Phase 3
0.8069	Intermediate Similarity	NPD3654	Approved
0.8059	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3610	Approved
0.8037	Intermediate Similarity	NPD3609	Approved
0.8036	Intermediate Similarity	NPD2096	Phase 2
0.8036	Intermediate Similarity	NPD2091	Phase 2
0.8026	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3476	Approved
0.8014	Intermediate Similarity	NPD3475	Approved
0.8012	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3961	Discontinued
0.7987	Intermediate Similarity	NPD7469	Discontinued
0.7977	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7948	Phase 1
0.7935	Intermediate Similarity	NPD4547	Phase 3
0.7931	Intermediate Similarity	NPD2118	Approved
0.7931	Intermediate Similarity	NPD2119	Approved
0.7931	Intermediate Similarity	NPD991	Phase 2
0.7931	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2006	Phase 2
0.7885	Intermediate Similarity	NPD2430	Phase 2
0.7879	Intermediate Similarity	NPD750	Phase 2
0.7874	Intermediate Similarity	NPD1038	Approved
0.7862	Intermediate Similarity	NPD2580	Discontinued
0.7852	Intermediate Similarity	NPD3385	Approved
0.784	Intermediate Similarity	NPD5140	Approved
0.784	Intermediate Similarity	NPD5138	Approved
0.7836	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6217	Discontinued
0.7834	Intermediate Similarity	NPD3833	Phase 3
0.7834	Intermediate Similarity	NPD3835	Phase 3
0.7829	Intermediate Similarity	NPD7618	Phase 3
0.7829	Intermediate Similarity	NPD7619	Phase 3
0.7821	Intermediate Similarity	NPD4703	Approved
0.7821	Intermediate Similarity	NPD4702	Approved
0.7805	Intermediate Similarity	NPD4639	Approved
0.7805	Intermediate Similarity	NPD4638	Approved
0.7805	Intermediate Similarity	NPD4640	Approved
0.7792	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2720	Phase 1
0.7791	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD802	Phase 2
0.7765	Intermediate Similarity	NPD5106	Approved
0.7765	Intermediate Similarity	NPD5105	Approved
0.7756	Intermediate Similarity	NPD1683	Approved
0.7751	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6664	Approved
0.7733	Intermediate Similarity	NPD4028	Approved
0.7733	Intermediate Similarity	NPD4029	Approved
0.7733	Intermediate Similarity	NPD4030	Approved
0.7714	Intermediate Similarity	NPD4615	Phase 2
0.7714	Intermediate Similarity	NPD3404	Approved
0.7711	Intermediate Similarity	NPD3117	Approved
0.7711	Intermediate Similarity	NPD3116	Approved
0.7707	Intermediate Similarity	NPD1661	Suspended
0.7702	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1262	Discovery
0.7697	Intermediate Similarity	NPD5021	Discontinued
0.7688	Intermediate Similarity	NPD2165	Phase 1
0.7679	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3115	Approved
0.764	Intermediate Similarity	NPD3113	Approved
0.764	Intermediate Similarity	NPD3112	Approved
0.764	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3114	Approved
0.7636	Intermediate Similarity	NPD1248	Discontinued
0.7625	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9583	Approved
0.7616	Intermediate Similarity	NPD3944	Approved
0.7616	Intermediate Similarity	NPD3942	Approved
0.7613	Intermediate Similarity	NPD5020	Approved
0.7609	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD1708	Approved
0.7602	Intermediate Similarity	NPD1707	Approved
0.7593	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3717	Discontinued
0.7561	Intermediate Similarity	NPD5315	Discontinued
0.7558	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5255	Approved
0.7545	Intermediate Similarity	NPD5436	Phase 1
0.7544	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD5901	Discontinued
0.7531	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8073	Approved
0.7517	Intermediate Similarity	NPD271	Approved
0.7517	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD268	Approved
0.7516	Intermediate Similarity	NPD3813	Approved
0.7514	Intermediate Similarity	NPD484	Approved
0.75	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1895	Discontinued
0.75	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8072	Approved
0.7485	Intermediate Similarity	NPD4326	Phase 2
0.7485	Intermediate Similarity	NPD8386	Phase 2
0.7484	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9357	Approved
0.7483	Intermediate Similarity	NPD9392	Approved
0.7483	Intermediate Similarity	NPD9396	Approved
0.7468	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3825	Phase 3
0.7453	Intermediate Similarity	NPD2882	Phase 1
0.7453	Intermediate Similarity	NPD6158	Phase 2
0.7453	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8093	Discontinued
0.7446	Intermediate Similarity	NPD8272	Phase 2
0.7439	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1183	Approved
0.7417	Intermediate Similarity	NPD715	Phase 3
0.7414	Intermediate Similarity	NPD7564	Discontinued
0.7407	Intermediate Similarity	NPD8094	Discontinued
0.7405	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7957	Phase 1
0.7401	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7470	Discontinued
0.7386	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2844	Phase 3
0.7372	Intermediate Similarity	NPD2070	Approved
0.7372	Intermediate Similarity	NPD2072	Approved
0.7372	Intermediate Similarity	NPD2071	Approved
0.7372	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2074	Approved
0.7372	Intermediate Similarity	NPD2068	Approved
0.7372	Intermediate Similarity	NPD2073	Approved
0.7372	Intermediate Similarity	NPD2075	Approved
0.7372	Intermediate Similarity	NPD2069	Approved
0.7368	Intermediate Similarity	NPD5100	Phase 3
0.7368	Intermediate Similarity	NPD803	Phase 1
0.7366	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD977	Approved
0.7362	Intermediate Similarity	NPD976	Approved
0.7362	Intermediate Similarity	NPD975	Approved
0.7355	Intermediate Similarity	NPD45	Approved
0.7355	Intermediate Similarity	NPD6554	Approved
0.7349	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4999	Phase 3
0.7333	Intermediate Similarity	NPD4998	Phase 3
0.733	Intermediate Similarity	NPD706	Phase 1
0.7322	Intermediate Similarity	NPD8248	Clinical (unspecified phase)

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