NPASS Compound

Structure

NPC135141 OpenBabel07101719142D 25 28 0 0 0 0 0 0 0 0999 V2000 -8.7782 -2.0418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0214 -2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6442 -1.5418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0269 -2.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9122 -1.5418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -1.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6442 -0.5418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3799 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1909 -0.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5218 0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5758 1.0408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1690 0.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9122 -0.5418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7782 -0.0418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5436 0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 1.1977 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5703 0.9363 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 -4.2346 -0.4965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 17 2 0 0 0 0 6 18 2 0 0 0 0 7 19 2 0 0 0 0 8 20 2 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 22 2 3 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	327.14
Volume:	350.326
LogP:	3.751
LogD:	3.953
LogS:	-4.409
# Rotatable Bonds:	5
TPSA:	61.01
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.749
Fsp3:	0.048
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.105
MDCK Permeability:	1.3861962543160189e-05
Pgp-inhibitor:	0.753
Pgp-substrate:	0.15
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.267
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.479
Plasma Protein Binding (PPB):	98.0476303100586%
Volume Distribution (VD):	0.628
Pgp-substrate:	1.3793376684188843%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.828
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.765
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	4.438
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.207
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.67
Rat Oral Acute Toxicity:	0.529
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.955
Carcinogencity:	0.073
Eye Corrosion:	0.005
Eye Irritation:	0.586
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC135141

Natural Product ID:	NPC135141
*Common Name:**	Chondriamide C
IUPAC Name:	(E)-3-(1H-indol-3-yl)-N-[(Z)-2-(1H-indol-3-yl)ethenyl]prop-2-enamide
Synonyms:	Chondriamide C
Standard InCHIKey:	UEIGNTNIVBVSQQ-PVHUKWJHSA-N
Standard InCHI:	InChI=1S/C21H17N3O/c25-21(10-9-15-13-23-19-7-3-1-5-17(15)19)22-12-11-16-14-24-20-8-4-2-6-18(16)20/h1-14,23-24H,(H,22,25)/b10-9+,12-11-
SMILES:	c1ccc2c(c1)c(/C=C/C(=N/C=Cc1c[nH]c3ccccc13)O)c[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456733
PubChem CID:	10336561
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868166]
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3503	Organism	Nippostrongylus brasiliensis	Nippostrongylus brasiliensis	EC50	=	90000.0	nM	PMID[474015]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	IC50	=	1000.0	nM	PMID[474016]

☑ 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 NPC135141 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	766
0.1-0.2	8850
0.2-0.3	17639
0.3-0.4	9118
0.4-0.5	2569
0.5-0.6	1800
0.6-0.7	1216
0.7-0.8	603
0.8-0.85	80
0.85-0.9	46
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92796
0.9384	High Similarity	NPC288838
0.9324	High Similarity	NPC53947
0.9324	High Similarity	NPC105818
0.9324	High Similarity	NPC24678
0.9315	High Similarity	NPC159856
0.9054	High Similarity	NPC314372
0.9048	High Similarity	NPC190296
0.902	High Similarity	NPC216643
0.8882	High Similarity	NPC59269
0.8824	High Similarity	NPC25008
0.8824	High Similarity	NPC73952
0.8824	High Similarity	NPC469763
0.8824	High Similarity	NPC469786
0.8824	High Similarity	NPC469760
0.8824	High Similarity	NPC469765
0.8824	High Similarity	NPC259644
0.8784	High Similarity	NPC469767
0.8784	High Similarity	NPC469768
0.8784	High Similarity	NPC469784
0.8784	High Similarity	NPC469783
0.8784	High Similarity	NPC469761
0.8784	High Similarity	NPC469779
0.8784	High Similarity	NPC469780
0.8767	High Similarity	NPC96102
0.8766	High Similarity	NPC80597
0.8766	High Similarity	NPC211572
0.8766	High Similarity	NPC70922
0.8766	High Similarity	NPC75540
0.8766	High Similarity	NPC212376
0.8725	High Similarity	NPC469766
0.8716	High Similarity	NPC73767
0.871	High Similarity	NPC469785
0.8707	High Similarity	NPC105127
0.8707	High Similarity	NPC84911
0.8701	High Similarity	NPC325903
0.8684	High Similarity	NPC471957
0.8671	High Similarity	NPC317105
0.8662	High Similarity	NPC131718
0.8654	High Similarity	NPC469762
0.8639	High Similarity	NPC29886
0.8639	High Similarity	NPC261195
0.8625	High Similarity	NPC63751
0.8591	High Similarity	NPC110126
0.8563	High Similarity	NPC15102
0.8562	High Similarity	NPC49217
0.8562	High Similarity	NPC469811
0.8533	High Similarity	NPC279081
0.8516	High Similarity	NPC216713
0.8506	High Similarity	NPC321911
0.8497	Intermediate Similarity	NPC63545
0.8493	Intermediate Similarity	NPC82295
0.8485	Intermediate Similarity	NPC176199
0.8485	Intermediate Similarity	NPC215795
0.8466	Intermediate Similarity	NPC477611
0.8457	Intermediate Similarity	NPC194411
0.8447	Intermediate Similarity	NPC474561
0.8447	Intermediate Similarity	NPC49954
0.8442	Intermediate Similarity	NPC179787
0.8442	Intermediate Similarity	NPC201380
0.8438	Intermediate Similarity	NPC311276
0.8438	Intermediate Similarity	NPC102423
0.8428	Intermediate Similarity	NPC279918
0.8412	Intermediate Similarity	NPC321708
0.8411	Intermediate Similarity	NPC230002
0.8405	Intermediate Similarity	NPC470498
0.8395	Intermediate Similarity	NPC201700
0.8387	Intermediate Similarity	NPC37548
0.8377	Intermediate Similarity	NPC143872
0.8375	Intermediate Similarity	NPC282231
0.8366	Intermediate Similarity	NPC242556
0.8344	Intermediate Similarity	NPC200214
0.8343	Intermediate Similarity	NPC308931
0.8343	Intermediate Similarity	NPC99939
0.8333	Intermediate Similarity	NPC160105
0.8323	Intermediate Similarity	NPC40779
0.8313	Intermediate Similarity	NPC44773
0.8313	Intermediate Similarity	NPC215584
0.8313	Intermediate Similarity	NPC284775
0.8303	Intermediate Similarity	NPC275305
0.8303	Intermediate Similarity	NPC37423
0.8302	Intermediate Similarity	NPC286427
0.828	Intermediate Similarity	NPC470233
0.8261	Intermediate Similarity	NPC470203
0.8253	Intermediate Similarity	NPC280852
0.825	Intermediate Similarity	NPC206819
0.825	Intermediate Similarity	NPC41257
0.825	Intermediate Similarity	NPC318065
0.825	Intermediate Similarity	NPC230869
0.825	Intermediate Similarity	NPC56765
0.8242	Intermediate Similarity	NPC313791
0.8239	Intermediate Similarity	NPC131887
0.8221	Intermediate Similarity	NPC54988
0.8214	Intermediate Similarity	NPC314919
0.821	Intermediate Similarity	NPC194640
0.8204	Intermediate Similarity	NPC68354
0.8199	Intermediate Similarity	NPC470204
0.8187	Intermediate Similarity	NPC236711
0.8176	Intermediate Similarity	NPC38736
0.8176	Intermediate Similarity	NPC477815
0.8176	Intermediate Similarity	NPC470507
0.8161	Intermediate Similarity	NPC324149
0.8153	Intermediate Similarity	NPC187951
0.8153	Intermediate Similarity	NPC124005
0.8151	Intermediate Similarity	NPC250361
0.8133	Intermediate Similarity	NPC314603
0.8129	Intermediate Similarity	NPC280290
0.8121	Intermediate Similarity	NPC475450
0.8118	Intermediate Similarity	NPC48938
0.8103	Intermediate Similarity	NPC476460
0.8095	Intermediate Similarity	NPC151939
0.8095	Intermediate Similarity	NPC248454
0.8086	Intermediate Similarity	NPC122141
0.8079	Intermediate Similarity	NPC227582
0.8067	Intermediate Similarity	NPC473930
0.8057	Intermediate Similarity	NPC99666
0.8054	Intermediate Similarity	NPC22079
0.805	Intermediate Similarity	NPC470823
0.8047	Intermediate Similarity	NPC213468
0.8041	Intermediate Similarity	NPC473762
0.8035	Intermediate Similarity	NPC17059
0.8026	Intermediate Similarity	NPC325252
0.8026	Intermediate Similarity	NPC218268
0.8011	Intermediate Similarity	NPC304203
0.8	Intermediate Similarity	NPC141926
0.8	Intermediate Similarity	NPC16659
0.8	Intermediate Similarity	NPC300688
0.7988	Intermediate Similarity	NPC90723
0.7987	Intermediate Similarity	NPC473587
0.7977	Intermediate Similarity	NPC94752
0.7975	Intermediate Similarity	NPC470111
0.7975	Intermediate Similarity	NPC229173
0.7974	Intermediate Similarity	NPC150259
0.7974	Intermediate Similarity	NPC251722
0.7974	Intermediate Similarity	NPC314102
0.7961	Intermediate Similarity	NPC198988
0.7952	Intermediate Similarity	NPC78020
0.795	Intermediate Similarity	NPC471458
0.795	Intermediate Similarity	NPC34844
0.7944	Intermediate Similarity	NPC106771
0.7944	Intermediate Similarity	NPC252338
0.7944	Intermediate Similarity	NPC23420
0.7944	Intermediate Similarity	NPC205254
0.7944	Intermediate Similarity	NPC303820
0.7941	Intermediate Similarity	NPC11126
0.7941	Intermediate Similarity	NPC265710
0.7935	Intermediate Similarity	NPC115611
0.7935	Intermediate Similarity	NPC59084
0.7935	Intermediate Similarity	NPC2949
0.7933	Intermediate Similarity	NPC67288
0.7933	Intermediate Similarity	NPC475428
0.7914	Intermediate Similarity	NPC474880
0.7914	Intermediate Similarity	NPC221786
0.7914	Intermediate Similarity	NPC475990
0.7911	Intermediate Similarity	NPC129042
0.791	Intermediate Similarity	NPC326422
0.7907	Intermediate Similarity	NPC163055
0.7907	Intermediate Similarity	NPC220765
0.7901	Intermediate Similarity	NPC52909
0.7901	Intermediate Similarity	NPC475935
0.7901	Intermediate Similarity	NPC184476
0.7901	Intermediate Similarity	NPC94211
0.7901	Intermediate Similarity	NPC141353
0.7886	Intermediate Similarity	NPC213629
0.7885	Intermediate Similarity	NPC63157
0.7885	Intermediate Similarity	NPC473868
0.7882	Intermediate Similarity	NPC473380
0.7882	Intermediate Similarity	NPC240088
0.7881	Intermediate Similarity	NPC256893
0.7881	Intermediate Similarity	NPC179365
0.7879	Intermediate Similarity	NPC8104
0.7877	Intermediate Similarity	NPC77555
0.7874	Intermediate Similarity	NPC171171
0.7871	Intermediate Similarity	NPC88097
0.787	Intermediate Similarity	NPC149155
0.787	Intermediate Similarity	NPC110500
0.787	Intermediate Similarity	NPC203468
0.7861	Intermediate Similarity	NPC204717
0.7861	Intermediate Similarity	NPC228835
0.7857	Intermediate Similarity	NPC125746
0.7857	Intermediate Similarity	NPC193761
0.7853	Intermediate Similarity	NPC299594
0.7853	Intermediate Similarity	NPC304187
0.7853	Intermediate Similarity	NPC477166
0.7849	Intermediate Similarity	NPC233936
0.7848	Intermediate Similarity	NPC470440
0.7833	Intermediate Similarity	NPC265576
0.7831	Intermediate Similarity	NPC274229
0.7824	Intermediate Similarity	NPC267885
0.7824	Intermediate Similarity	NPC474958
0.7818	Intermediate Similarity	NPC225018
0.7816	Intermediate Similarity	NPC314002
0.7803	Intermediate Similarity	NPC83381
0.7799	Intermediate Similarity	NPC316069
0.7798	Intermediate Similarity	NPC97343
0.7791	Intermediate Similarity	NPC285469
0.779	Intermediate Similarity	NPC74413
0.7764	Intermediate Similarity	NPC40070
0.776	Intermediate Similarity	NPC476073
0.7759	Intermediate Similarity	NPC284678

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 NPC135141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	760
0.2-0.3	882
0.3-0.4	1793
0.4-0.5	2429
0.5-0.6	1825
0.6-0.7	886
0.7-0.8	241
0.8-0.85	7
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD5069	Clinical (unspecified phase)
0.8816	High Similarity	NPD4463	Approved
0.8816	High Similarity	NPD4462	Approved
0.8773	High Similarity	NPD6595	Phase 3
0.8767	High Similarity	NPD198	Clinical (unspecified phase)
0.8765	High Similarity	NPD6203	Clinical (unspecified phase)
0.8758	High Similarity	NPD5065	Approved
0.875	High Similarity	NPD4374	Clinical (unspecified phase)
0.8725	High Similarity	NPD1722	Approved
0.8716	High Similarity	NPD786	Approved
0.8693	High Similarity	NPD2172	Phase 1
0.8563	High Similarity	NPD6610	Clinical (unspecified phase)
0.8506	High Similarity	NPD3100	Discontinued
0.8462	Intermediate Similarity	NPD2837	Discontinued
0.8232	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD2639	Approved
0.8221	Intermediate Similarity	NPD2642	Approved
0.821	Intermediate Similarity	NPD3323	Discontinued
0.8204	Intermediate Similarity	NPD3505	Approved
0.8204	Intermediate Similarity	NPD3506	Approved
0.8193	Intermediate Similarity	NPD4128	Approved
0.8171	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD4079	Approved
0.8155	Intermediate Similarity	NPD4076	Approved
0.8148	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4181	Approved
0.8095	Intermediate Similarity	NPD2144	Approved
0.8081	Intermediate Similarity	NPD6217	Discontinued
0.8059	Intermediate Similarity	NPD1895	Discontinued
0.8036	Intermediate Similarity	NPD4075	Phase 2
0.8035	Intermediate Similarity	NPD8431	Approved
0.8013	Intermediate Similarity	NPD5254	Discontinued
0.8012	Intermediate Similarity	NPD5105	Approved
0.8012	Intermediate Similarity	NPD5106	Approved
0.8011	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3833	Phase 3
0.7987	Intermediate Similarity	NPD3835	Phase 3
0.7978	Intermediate Similarity	NPD7948	Phase 1
0.7975	Intermediate Similarity	NPD1404	Approved
0.7975	Intermediate Similarity	NPD1403	Approved
0.7953	Intermediate Similarity	NPD3038	Discontinued
0.7952	Intermediate Similarity	NPD2640	Approved
0.7952	Intermediate Similarity	NPD2641	Approved
0.7949	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD1326	Approved
0.7904	Intermediate Similarity	NPD1325	Approved
0.7898	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD482	Approved
0.7862	Intermediate Similarity	NPD4547	Phase 3
0.7857	Intermediate Similarity	NPD3610	Approved
0.7857	Intermediate Similarity	NPD3609	Approved
0.7844	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2006	Phase 2
0.7831	Intermediate Similarity	NPD2720	Phase 1
0.7831	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3961	Discontinued
0.7824	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2430	Phase 2
0.7803	Intermediate Similarity	NPD2095	Phase 2
0.7803	Intermediate Similarity	NPD2094	Phase 2
0.7803	Intermediate Similarity	NPD2092	Phase 2
0.7799	Intermediate Similarity	NPD7469	Discontinued
0.7778	Intermediate Similarity	NPD3385	Approved
0.7772	Intermediate Similarity	NPD5426	Phase 3
0.7771	Intermediate Similarity	NPD1592	Phase 3
0.7771	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2091	Phase 2
0.7759	Intermediate Similarity	NPD2096	Phase 2
0.7759	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD3404	Approved
0.7746	Intermediate Similarity	NPD1707	Approved
0.7746	Intermediate Similarity	NPD1708	Approved
0.7742	Intermediate Similarity	NPD1262	Discovery
0.7738	Intermediate Similarity	NPD5021	Discontinued
0.7733	Intermediate Similarity	NPD991	Phase 2
0.7733	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3476	Approved
0.7697	Intermediate Similarity	NPD3475	Approved
0.7667	Intermediate Similarity	NPD7619	Phase 3
0.7667	Intermediate Similarity	NPD7618	Phase 3
0.7654	Intermediate Similarity	NPD4615	Phase 2
0.7636	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4326	Phase 2
0.7633	Intermediate Similarity	NPD4639	Approved
0.7633	Intermediate Similarity	NPD4640	Approved
0.7633	Intermediate Similarity	NPD4638	Approved
0.7633	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3654	Approved
0.7624	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2119	Approved
0.7616	Intermediate Similarity	NPD2118	Approved
0.761	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5436	Phase 1
0.7581	Intermediate Similarity	NPD5901	Discontinued
0.7578	Intermediate Similarity	NPD1683	Approved
0.7576	Intermediate Similarity	NPD2580	Discontinued
0.7576	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3813	Approved
0.756	Intermediate Similarity	NPD5140	Approved
0.756	Intermediate Similarity	NPD5138	Approved
0.7545	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4703	Approved
0.7531	Intermediate Similarity	NPD1661	Suspended
0.7531	Intermediate Similarity	NPD4702	Approved
0.7527	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7470	Discontinued
0.7526	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6554	Approved
0.7516	Intermediate Similarity	NPD45	Approved
0.7514	Intermediate Similarity	NPD1038	Approved
0.7514	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3825	Phase 3
0.75	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6158	Phase 2
0.75	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD750	Phase 2
0.75	Intermediate Similarity	NPD6999	Discontinued
0.7487	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6664	Approved
0.7474	Intermediate Similarity	NPD3843	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3116	Approved
0.7442	Intermediate Similarity	NPD3117	Approved
0.7436	Intermediate Similarity	NPD4030	Approved
0.7436	Intermediate Similarity	NPD4028	Approved
0.7436	Intermediate Similarity	NPD4029	Approved
0.7433	Intermediate Similarity	NPD4886	Phase 2
0.7432	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD803	Phase 1
0.7418	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD802	Phase 2
0.7414	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2165	Phase 1
0.7407	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8093	Discontinued
0.7394	Intermediate Similarity	NPD2882	Phase 1
0.7382	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8073	Approved
0.7374	Intermediate Similarity	NPD2793	Discontinued
0.7365	Intermediate Similarity	NPD3115	Approved
0.7365	Intermediate Similarity	NPD3113	Approved
0.7365	Intermediate Similarity	NPD3112	Approved
0.7365	Intermediate Similarity	NPD3114	Approved
0.736	Intermediate Similarity	NPD4957	Phase 2
0.736	Intermediate Similarity	NPD7564	Discontinued
0.7358	Intermediate Similarity	NPD8094	Discontinued
0.7349	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8072	Approved
0.7333	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8386	Phase 2
0.7329	Intermediate Similarity	NPD5020	Approved
0.7325	Intermediate Similarity	NPD3942	Approved
0.7325	Intermediate Similarity	NPD3944	Approved
0.7322	Intermediate Similarity	NPD2717	Phase 2
0.7297	Intermediate Similarity	NPD2880	Discontinued
0.7297	Intermediate Similarity	NPD3830	Phase 1
0.7294	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5315	Discontinued
0.7287	Intermediate Similarity	NPD3015	Discontinued
0.7283	Intermediate Similarity	NPD4998	Phase 3
0.7283	Intermediate Similarity	NPD4999	Phase 3
0.7278	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5255	Approved
0.7278	Intermediate Similarity	NPD706	Phase 1
0.7278	Intermediate Similarity	NPD4880	Discontinued
0.7277	Intermediate Similarity	NPD2510	Approved
0.7277	Intermediate Similarity	NPD2509	Approved
0.7273	Intermediate Similarity	NPD1183	Approved
0.7273	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD484	Approved
0.7267	Intermediate Similarity	NPD1248	Discontinued
0.7263	Intermediate Similarity	NPD7001	Phase 3
0.7263	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5892	Approved
0.7263	Intermediate Similarity	NPD2008	Discontinued
0.7263	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7957	Phase 1
0.7263	Intermediate Similarity	NPD6178	Phase 3

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