NPASS Compound

Structure

CID322064 OpenBabel06191716162D 28 31 0 0 0 0 0 0 0 0999 V2000 -0.3968 2.8467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -2.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -2.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8518 2.5719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5400 1.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7441 2.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4323 1.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8574 1.2031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0672 1.7772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7498 1.6005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5344 2.3951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6926 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 1.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3847 1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1749 1.3799 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 1.6923 1.9543 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5737 1.1641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4267 2.7924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4867 2.9255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 16 2 0 0 0 0 5 18 2 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 26 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 19 25 2 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.14
Volume:	385.202
LogP:	3.519
LogD:	3.592
LogS:	-4.474
# Rotatable Bonds:	6
TPSA:	95.08
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	2.343
Fsp3:	0.136
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175
MDCK Permeability:	6.24673202764825e-06
Pgp-inhibitor:	0.46
Pgp-substrate:	0.243
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	96.9447021484375%
Volume Distribution (VD):	0.693
Pgp-substrate:	1.3824419975280762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.872
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	5.967
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.507
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.366
Carcinogencity:	0.168
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC322064

Natural Product ID:	NPC322064
*Common Name:**	4'-O-Desmethyl Marinacarboline A
IUPAC Name:	1-acetyl-N-[2-(4-hydroxyphenyl)ethyl]-9H-pyrido[3,4-b]indole-3-carboxamide
Synonyms:	4'-O-Desmethyl Marinacarboline A
Standard InCHIKey:	XHHABJFVNYNXCX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H19N3O3/c1-13(26)20-21-17(16-4-2-3-5-18(16)24-21)12-19(25-20)22(28)23-11-10-14-6-8-15(27)9-7-14/h2-9,12,24,27H,10-11H2,1H3,(H,23,28)
SMILES:	Oc1ccc(cc1)CCNC(=O)c1nc(C(=O)C)c2c(c1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928401
PubChem CID:	56599000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO31006	Marinactinospora thermotolerans	Species	0cardiopsaceae	Bacteria	n.a.	spore	n.a.	PMID[21977916]
NPO31006	Marinactinospora thermotolerans	Species	0cardiopsaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21977916]

☑ 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	10

Activity Type	# Activity
Cell Line	8
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[507225]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	16650.0	nM	PMID[507225]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	15590.0	nM	PMID[507225]

☑ 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 NPC322064 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	414
0.1-0.2	3246
0.2-0.3	13407
0.3-0.4	7616
0.4-0.5	12817
0.5-0.6	2613
0.6-0.7	2048
0.7-0.8	498
0.8-0.85	32
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.93	High Similarity	NPC323969
0.9055	High Similarity	NPC27041
0.8796	High Similarity	NPC324091
0.8607	High Similarity	NPC270918
0.8505	High Similarity	NPC279189
0.8505	High Similarity	NPC200553
0.845	Intermediate Similarity	NPC471944
0.8419	Intermediate Similarity	NPC207686
0.8389	Intermediate Similarity	NPC220851
0.8387	Intermediate Similarity	NPC162002
0.8341	Intermediate Similarity	NPC174489
0.8299	Intermediate Similarity	NPC133003
0.8276	Intermediate Similarity	NPC317701
0.8265	Intermediate Similarity	NPC26641
0.822	Intermediate Similarity	NPC151635
0.82	Intermediate Similarity	NPC79356
0.82	Intermediate Similarity	NPC102592
0.819	Intermediate Similarity	NPC37152
0.8178	Intermediate Similarity	NPC229893
0.8145	Intermediate Similarity	NPC101350
0.8141	Intermediate Similarity	NPC324149
0.8134	Intermediate Similarity	NPC110182
0.81	Intermediate Similarity	NPC235685
0.8075	Intermediate Similarity	NPC269270
0.8069	Intermediate Similarity	NPC141454
0.8057	Intermediate Similarity	NPC477979
0.8037	Intermediate Similarity	NPC14686
0.8037	Intermediate Similarity	NPC276657
0.8018	Intermediate Similarity	NPC91868
0.8018	Intermediate Similarity	NPC63971
0.8009	Intermediate Similarity	NPC122436
0.8009	Intermediate Similarity	NPC178858
0.798	Intermediate Similarity	NPC74153
0.7973	Intermediate Similarity	NPC477549
0.7945	Intermediate Similarity	NPC194740
0.7923	Intermediate Similarity	NPC476098
0.7923	Intermediate Similarity	NPC165599
0.7885	Intermediate Similarity	NPC132539
0.7864	Intermediate Similarity	NPC471762
0.7864	Intermediate Similarity	NPC66777
0.786	Intermediate Similarity	NPC264285
0.7848	Intermediate Similarity	NPC182222
0.7848	Intermediate Similarity	NPC97902
0.7847	Intermediate Similarity	NPC175602
0.7837	Intermediate Similarity	NPC134848
0.7835	Intermediate Similarity	NPC252572
0.7833	Intermediate Similarity	NPC326422
0.7833	Intermediate Similarity	NPC473821
0.7822	Intermediate Similarity	NPC476460
0.782	Intermediate Similarity	NPC61038
0.7805	Intermediate Similarity	NPC473814
0.7805	Intermediate Similarity	NPC78767
0.7778	Intermediate Similarity	NPC191415
0.7767	Intermediate Similarity	NPC474916
0.7758	Intermediate Similarity	NPC132329
0.7746	Intermediate Similarity	NPC23294
0.7738	Intermediate Similarity	NPC157931
0.7738	Intermediate Similarity	NPC257851
0.7731	Intermediate Similarity	NPC305984
0.7725	Intermediate Similarity	NPC244741
0.7725	Intermediate Similarity	NPC183777
0.7723	Intermediate Similarity	NPC221873
0.7714	Intermediate Similarity	NPC472259
0.7714	Intermediate Similarity	NPC470500
0.7713	Intermediate Similarity	NPC260434
0.7707	Intermediate Similarity	NPC93390
0.77	Intermediate Similarity	NPC303951
0.7692	Intermediate Similarity	NPC24370
0.7692	Intermediate Similarity	NPC319232
0.7689	Intermediate Similarity	NPC39679
0.7685	Intermediate Similarity	NPC330009
0.7681	Intermediate Similarity	NPC306376
0.7674	Intermediate Similarity	NPC207866
0.7669	Intermediate Similarity	NPC74619
0.7668	Intermediate Similarity	NPC326363
0.7667	Intermediate Similarity	NPC223427
0.765	Intermediate Similarity	NPC312645
0.7644	Intermediate Similarity	NPC284888
0.7636	Intermediate Similarity	NPC16352
0.763	Intermediate Similarity	NPC475070
0.7627	Intermediate Similarity	NPC63109
0.7626	Intermediate Similarity	NPC272174
0.7624	Intermediate Similarity	NPC17273
0.7624	Intermediate Similarity	NPC135601
0.7624	Intermediate Similarity	NPC141612
0.7615	Intermediate Similarity	NPC303658
0.7613	Intermediate Similarity	NPC214142
0.7612	Intermediate Similarity	NPC477003
0.7611	Intermediate Similarity	NPC325976
0.7606	Intermediate Similarity	NPC86834
0.7606	Intermediate Similarity	NPC266249
0.7606	Intermediate Similarity	NPC210828
0.76	Intermediate Similarity	NPC477516
0.7593	Intermediate Similarity	NPC89508
0.7586	Intermediate Similarity	NPC206186
0.7583	Intermediate Similarity	NPC53144
0.7581	Intermediate Similarity	NPC9894
0.7578	Intermediate Similarity	NPC118559
0.7578	Intermediate Similarity	NPC304307
0.7578	Intermediate Similarity	NPC124920
0.7578	Intermediate Similarity	NPC34580
0.7578	Intermediate Similarity	NPC261251
0.7569	Intermediate Similarity	NPC293151
0.7562	Intermediate Similarity	NPC470205
0.7556	Intermediate Similarity	NPC119006
0.7553	Intermediate Similarity	NPC258048
0.7546	Intermediate Similarity	NPC219087
0.7545	Intermediate Similarity	NPC100547
0.7544	Intermediate Similarity	NPC15801
0.7544	Intermediate Similarity	NPC184225
0.7536	Intermediate Similarity	NPC57398
0.7535	Intermediate Similarity	NPC123839
0.7525	Intermediate Similarity	NPC21429
0.7523	Intermediate Similarity	NPC171787
0.7523	Intermediate Similarity	NPC469928
0.7522	Intermediate Similarity	NPC196718
0.7521	Intermediate Similarity	NPC165964
0.7511	Intermediate Similarity	NPC60621
0.7511	Intermediate Similarity	NPC322135
0.7511	Intermediate Similarity	NPC53534
0.7511	Intermediate Similarity	NPC474896
0.7511	Intermediate Similarity	NPC223409
0.7511	Intermediate Similarity	NPC95240
0.75	Intermediate Similarity	NPC87413
0.75	Intermediate Similarity	NPC478078
0.7489	Intermediate Similarity	NPC323752
0.7478	Intermediate Similarity	NPC14288
0.7477	Intermediate Similarity	NPC283117
0.7477	Intermediate Similarity	NPC478141
0.7477	Intermediate Similarity	NPC31097
0.7475	Intermediate Similarity	NPC243058
0.7475	Intermediate Similarity	NPC161861
0.7475	Intermediate Similarity	NPC102755
0.7466	Intermediate Similarity	NPC150239
0.7465	Intermediate Similarity	NPC118940
0.7464	Intermediate Similarity	NPC227582
0.7462	Intermediate Similarity	NPC471943
0.7454	Intermediate Similarity	NPC5145
0.7453	Intermediate Similarity	NPC211813
0.7452	Intermediate Similarity	NPC276517
0.7445	Intermediate Similarity	NPC102593
0.7445	Intermediate Similarity	NPC321592
0.7445	Intermediate Similarity	NPC54803
0.7443	Intermediate Similarity	NPC3207
0.744	Intermediate Similarity	NPC99666
0.7438	Intermediate Similarity	NPC203635
0.7435	Intermediate Similarity	NPC470784
0.7431	Intermediate Similarity	NPC31700
0.7429	Intermediate Similarity	NPC131887
0.7425	Intermediate Similarity	NPC160898
0.7424	Intermediate Similarity	NPC35042
0.7421	Intermediate Similarity	NPC288987
0.7419	Intermediate Similarity	NPC82370
0.7418	Intermediate Similarity	NPC200836
0.7415	Intermediate Similarity	NPC473800
0.7415	Intermediate Similarity	NPC181081
0.7415	Intermediate Similarity	NPC278434
0.7412	Intermediate Similarity	NPC323198
0.7404	Intermediate Similarity	NPC304203
0.7398	Intermediate Similarity	NPC115232
0.7395	Intermediate Similarity	NPC53344
0.7391	Intermediate Similarity	NPC184680
0.7385	Intermediate Similarity	NPC12344
0.738	Intermediate Similarity	NPC33064
0.738	Intermediate Similarity	NPC245055
0.7379	Intermediate Similarity	NPC473666
0.7376	Intermediate Similarity	NPC91179
0.7376	Intermediate Similarity	NPC247803
0.7373	Intermediate Similarity	NPC85273
0.7366	Intermediate Similarity	NPC51388
0.7366	Intermediate Similarity	NPC90415
0.7363	Intermediate Similarity	NPC284775
0.7359	Intermediate Similarity	NPC470785
0.7358	Intermediate Similarity	NPC315491
0.7358	Intermediate Similarity	NPC45459
0.7358	Intermediate Similarity	NPC252338
0.7358	Intermediate Similarity	NPC213308
0.7348	Intermediate Similarity	NPC473187
0.7342	Intermediate Similarity	NPC74360
0.7342	Intermediate Similarity	NPC48317
0.7342	Intermediate Similarity	NPC193267
0.7342	Intermediate Similarity	NPC213530
0.7339	Intermediate Similarity	NPC294375
0.733	Intermediate Similarity	NPC469727
0.7327	Intermediate Similarity	NPC72980
0.7327	Intermediate Similarity	NPC219336
0.7325	Intermediate Similarity	NPC152620
0.7321	Intermediate Similarity	NPC472210
0.7321	Intermediate Similarity	NPC247735
0.7321	Intermediate Similarity	NPC472295
0.7321	Intermediate Similarity	NPC269886
0.7321	Intermediate Similarity	NPC81802
0.7318	Intermediate Similarity	NPC50562
0.7318	Intermediate Similarity	NPC118228
0.7318	Intermediate Similarity	NPC237740
0.7317	Intermediate Similarity	NPC241025
0.7315	Intermediate Similarity	NPC4687
0.7315	Intermediate Similarity	NPC321428
0.7315	Intermediate Similarity	NPC249583
0.7311	Intermediate Similarity	NPC476167

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 NPC322064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	627
0.2-0.3	862
0.3-0.4	1229
0.4-0.5	2754
0.5-0.6	2221
0.6-0.7	1111
0.7-0.8	99
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD6376	Discontinued
0.8028	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7936	Intermediate Similarity	NPD7603	Discontinued
0.7734	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3243	Approved
0.7664	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4845	Discontinued
0.7655	Intermediate Similarity	NPD7853	Phase 2
0.7559	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2951	Discontinued
0.7523	Intermediate Similarity	NPD2916	Discontinued
0.75	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4558	Phase 2
0.7477	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5901	Discontinued
0.7464	Intermediate Similarity	NPD7948	Phase 1
0.7445	Intermediate Similarity	NPD4885	Approved
0.7444	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3962	Phase 2
0.7425	Intermediate Similarity	NPD3959	Phase 2
0.7422	Intermediate Similarity	NPD7994	Phase 2
0.7403	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5293	Phase 2
0.7391	Intermediate Similarity	NPD4368	Phase 2
0.7373	Intermediate Similarity	NPD5482	Discontinued
0.7358	Intermediate Similarity	NPD484	Approved
0.7357	Intermediate Similarity	NPD5479	Discontinued
0.733	Intermediate Similarity	NPD4948	Discontinued
0.7309	Intermediate Similarity	NPD6242	Discontinued
0.7304	Intermediate Similarity	NPD3319	Phase 1
0.7304	Intermediate Similarity	NPD3318	Approved
0.7304	Intermediate Similarity	NPD3320	Approved
0.7302	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3263	Phase 3
0.7296	Intermediate Similarity	NPD6790	Phase 1
0.7293	Intermediate Similarity	NPD3746	Discontinued
0.7291	Intermediate Similarity	NPD5445	Approved
0.7286	Intermediate Similarity	NPD7619	Phase 3
0.7286	Intermediate Similarity	NPD7618	Phase 3
0.7285	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5416	Discontinued
0.7256	Intermediate Similarity	NPD6176	Phase 1
0.7252	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7817	Phase 1
0.7243	Intermediate Similarity	NPD7727	Phase 2
0.7243	Intermediate Similarity	NPD4511	Phase 1
0.7238	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8093	Discontinued
0.7222	Intermediate Similarity	NPD8115	Approved
0.7222	Intermediate Similarity	NPD8114	Approved
0.722	Intermediate Similarity	NPD4429	Discontinued
0.7215	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3394	Approved
0.7207	Intermediate Similarity	NPD3393	Approved
0.7207	Intermediate Similarity	NPD3389	Approved
0.7202	Intermediate Similarity	NPD2510	Approved
0.7202	Intermediate Similarity	NPD2443	Approved
0.7202	Intermediate Similarity	NPD2509	Approved
0.7202	Intermediate Similarity	NPD2442	Approved
0.7198	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6164	Phase 2
0.7193	Intermediate Similarity	NPD6165	Phase 2
0.7183	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5065	Approved
0.7176	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5850	Phase 3
0.715	Intermediate Similarity	NPD6999	Discontinued
0.715	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD8289	Discontinued
0.7143	Intermediate Similarity	NPD5426	Phase 3
0.7131	Intermediate Similarity	NPD6531	Approved
0.7131	Intermediate Similarity	NPD6530	Approved
0.713	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5473	Discontinued
0.7117	Intermediate Similarity	NPD8094	Discontinued
0.7117	Intermediate Similarity	NPD3945	Discontinued
0.7115	Intermediate Similarity	NPD7181	Phase 3
0.7112	Intermediate Similarity	NPD4373	Phase 2
0.7111	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4922	Phase 2
0.7105	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6209	Approved
0.7087	Intermediate Similarity	NPD3178	Discontinued
0.7085	Intermediate Similarity	NPD4897	Phase 2
0.7085	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5017	Discontinued
0.7083	Intermediate Similarity	NPD3986	Discontinued
0.7083	Intermediate Similarity	NPD5552	Discontinued
0.708	Intermediate Similarity	NPD7689	Approved
0.707	Intermediate Similarity	NPD3814	Phase 1
0.7069	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5632	Approved
0.7067	Intermediate Similarity	NPD7878	Phase 2
0.7067	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4952	Phase 3
0.7056	Intermediate Similarity	NPD5022	Discontinued
0.7048	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD6716	Phase 1
0.7045	Intermediate Similarity	NPD7666	Phase 3
0.7045	Intermediate Similarity	NPD7665	Phase 2
0.7043	Intermediate Similarity	NPD3259	Approved
0.7039	Intermediate Similarity	NPD4850	Phase 1
0.7037	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5809	Phase 3
0.7032	Intermediate Similarity	NPD7568	Phase 1
0.7032	Intermediate Similarity	NPD2008	Discontinued
0.7032	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6159	Phase 2
0.7019	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6995	Phase 1
0.7018	Intermediate Similarity	NPD8356	Approved
0.7016	Intermediate Similarity	NPD5450	Discontinued
0.7014	Intermediate Similarity	NPD2408	Discontinued
0.7009	Intermediate Similarity	NPD4848	Phase 1
0.7005	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8322	Phase 2
0.7	Intermediate Similarity	NPD8349	Phase 1
0.6996	Remote Similarity	NPD8463	Approved
0.6996	Remote Similarity	NPD5866	Approved
0.6996	Remote Similarity	NPD2411	Approved
0.6996	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7395	Discontinued
0.699	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6752	Phase 1
0.6987	Remote Similarity	NPD6753	Phase 1
0.6987	Remote Similarity	NPD6173	Approved
0.6986	Remote Similarity	NPD3947	Discontinued
0.6981	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4462	Approved
0.6974	Remote Similarity	NPD4463	Approved
0.697	Remote Similarity	NPD8430	Approved
0.6968	Remote Similarity	NPD5658	Approved
0.6963	Remote Similarity	NPD4400	Approved
0.696	Remote Similarity	NPD5198	Approved
0.696	Remote Similarity	NPD6770	Approved
0.696	Remote Similarity	NPD5199	Approved
0.6959	Remote Similarity	NPD4601	Approved
0.6959	Remote Similarity	NPD4600	Approved
0.6951	Remote Similarity	NPD7470	Discontinued
0.6948	Remote Similarity	NPD5937	Approved
0.6946	Remote Similarity	NPD1325	Approved
0.6946	Remote Similarity	NPD1326	Approved
0.6943	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2882	Phase 1
0.6938	Remote Similarity	NPD7564	Discontinued
0.6938	Remote Similarity	NPD1096	Discontinued
0.6931	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7180	Phase 3
0.693	Remote Similarity	NPD5512	Phase 3
0.6927	Remote Similarity	NPD6492	Phase 2
0.6927	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7867	Phase 1
0.692	Remote Similarity	NPD7656	Approved
0.692	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7657	Approved
0.6915	Remote Similarity	NPD1631	Approved
0.6912	Remote Similarity	NPD6248	Phase 2
0.6912	Remote Similarity	NPD7308	Discontinued
0.6912	Remote Similarity	NPD6249	Phase 2
0.6911	Remote Similarity	NPD8091	Phase 3
0.6909	Remote Similarity	NPD6987	Phase 1
0.6908	Remote Similarity	NPD6456	Discontinued
0.6904	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5507	Approved
0.69	Remote Similarity	NPD5506	Approved
0.6898	Remote Similarity	NPD6664	Approved
0.6897	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2844	Phase 3
0.6895	Remote Similarity	NPD7187	Phase 2
0.6893	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4334	Discontinued
0.6886	Remote Similarity	NPD3258	Approved
0.6881	Remote Similarity	NPD4500	Approved
0.6881	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4501	Approved
0.6878	Remote Similarity	NPD3507	Phase 2
0.6872	Remote Similarity	NPD3315	Phase 3
0.6872	Remote Similarity	NPD6710	Phase 3
0.687	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4506	Discontinued
0.686	Remote Similarity	NPD7996	Phase 2
0.6858	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5827	Discontinued
0.6854	Remote Similarity	NPD4499	Approved
0.6853	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6158	Phase 2

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