NPASS Compound

Structure

CID317701 OpenBabel06191716142D 30 34 0 0 0 0 0 0 0 0999 V2000 0.5183 1.4928 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 1.8919 -4.2967 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 2.8055 -3.8900 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 1.0829 -3.7089 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 2.9100 -2.8955 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 -0.4817 -1.9713 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 1.0183 0.6268 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 1.1875 -2.7144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5183 -1.9713 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 2.1010 -2.3077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9817 -1.1052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5183 -0.2392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0183 -1.1052 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 1.9965 -1.3131 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4817 -0.2392 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0183 0.6268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 5.4223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 19 2 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 26 1 0 0 0 0 14 22 1 0 0 0 0 14 29 2 0 0 0 0 15 16 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 28 2 0 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	410.808
LogP:	4.182
LogD:	3.926
LogS:	-4.548
# Rotatable Bonds:	6
TPSA:	90.64
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	2.443
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.299
MDCK Permeability:	4.778134098160081e-06
Pgp-inhibitor:	0.997
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.454
Plasma Protein Binding (PPB):	97.70818328857422%
Volume Distribution (VD):	1.039
Pgp-substrate:	1.0930589437484741%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.936
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.84
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	3.727
Half-life (T1/2):	0.348

ADMET: Toxicity

hERG Blockers:	0.229
Human Hepatotoxicity (H-HT):	0.891
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.256
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.64
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC317701

Natural Product ID:	NPC317701
*Common Name:**	Marinacarboline D
IUPAC Name:	1-acetyl-N-[2-(1H-indol-3-yl)ethyl]-9H-pyrido[3,4-b]indole-3-carboxamide
Synonyms:	Marinacarboline D
Standard InCHIKey:	PCOBOAPRWGQQGA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H20N4O2/c1-14(29)22-23-18(17-7-3-5-9-20(17)27-23)12-21(28-22)24(30)25-11-10-15-13-26-19-8-4-2-6-16(15)19/h2-9,12-13,26-27H,10-11H2,1H3,(H,25,30)
SMILES:	CC(=O)C1=C2C(=CC(=N1)C(=O)NCCC3=CNC4=CC=CC=C43)C5=CC=CC=C5N2
Synthetic Gene Cluster:	BGC0001137;
ChEMBL Identifier:	CHEMBL1928403
PubChem CID:	56599001
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[552979]
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[552979]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5390.0	nM	PMID[552979]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3590.0	nM	PMID[552979]

☑ 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 NPC317701 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	591
0.1-0.2	5564
0.2-0.3	16882
0.3-0.4	13615
0.4-0.5	2097
0.5-0.6	1877
0.6-0.7	1468
0.7-0.8	533
0.8-0.85	38
0.85-0.9	16
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9392	High Similarity	NPC326422
0.9333	High Similarity	NPC324091
0.9282	High Similarity	NPC476460
0.8944	High Similarity	NPC191415
0.8846	High Similarity	NPC477003
0.8798	High Similarity	NPC133003
0.8778	High Similarity	NPC284775
0.877	High Similarity	NPC304203
0.8722	High Similarity	NPC151635
0.8677	High Similarity	NPC102592
0.8677	High Similarity	NPC79356
0.8595	High Similarity	NPC99939
0.8595	High Similarity	NPC308931
0.8587	High Similarity	NPC102755
0.8571	High Similarity	NPC116555
0.8439	Intermediate Similarity	NPC229893
0.8351	Intermediate Similarity	NPC237414
0.8342	Intermediate Similarity	NPC167710
0.8306	Intermediate Similarity	NPC252572
0.8289	Intermediate Similarity	NPC470205
0.8276	Intermediate Similarity	NPC322064
0.8256	Intermediate Similarity	NPC477004
0.8235	Intermediate Similarity	NPC267811
0.8207	Intermediate Similarity	NPC161861
0.8197	Intermediate Similarity	NPC471943
0.8168	Intermediate Similarity	NPC473666
0.8116	Intermediate Similarity	NPC323969
0.8103	Intermediate Similarity	NPC128244
0.8063	Intermediate Similarity	NPC135601
0.8063	Intermediate Similarity	NPC141612
0.8063	Intermediate Similarity	NPC17273
0.8061	Intermediate Similarity	NPC227582
0.8058	Intermediate Similarity	NPC27041
0.8	Intermediate Similarity	NPC117027
0.7991	Intermediate Similarity	NPC207686
0.798	Intermediate Similarity	NPC268744
0.798	Intermediate Similarity	NPC220797
0.798	Intermediate Similarity	NPC475914
0.798	Intermediate Similarity	NPC74413
0.798	Intermediate Similarity	NPC201266
0.798	Intermediate Similarity	NPC153123
0.798	Intermediate Similarity	NPC474318
0.7978	Intermediate Similarity	NPC317105
0.7972	Intermediate Similarity	NPC101350
0.7968	Intermediate Similarity	NPC469529
0.7958	Intermediate Similarity	NPC21429
0.7951	Intermediate Similarity	NPC473218
0.7951	Intermediate Similarity	NPC470702
0.794	Intermediate Similarity	NPC166209
0.794	Intermediate Similarity	NPC13456
0.794	Intermediate Similarity	NPC252338
0.794	Intermediate Similarity	NPC77241
0.794	Intermediate Similarity	NPC269203
0.7937	Intermediate Similarity	NPC11126
0.7927	Intermediate Similarity	NPC17059
0.7926	Intermediate Similarity	NPC235685
0.7913	Intermediate Similarity	NPC470703
0.7895	Intermediate Similarity	NPC16659
0.7892	Intermediate Similarity	NPC56233
0.7889	Intermediate Similarity	NPC81535
0.7889	Intermediate Similarity	NPC325903
0.788	Intermediate Similarity	NPC478182
0.7876	Intermediate Similarity	NPC94752
0.7865	Intermediate Similarity	NPC228835
0.7864	Intermediate Similarity	NPC153980
0.7864	Intermediate Similarity	NPC471193
0.7864	Intermediate Similarity	NPC6865
0.7864	Intermediate Similarity	NPC471194
0.7861	Intermediate Similarity	NPC260900
0.7857	Intermediate Similarity	NPC216550
0.7843	Intermediate Similarity	NPC266249
0.7842	Intermediate Similarity	NPC265710
0.7838	Intermediate Similarity	NPC233380
0.7838	Intermediate Similarity	NPC42372
0.7838	Intermediate Similarity	NPC115232
0.7831	Intermediate Similarity	NPC280852
0.7816	Intermediate Similarity	NPC72956
0.7811	Intermediate Similarity	NPC471944
0.7801	Intermediate Similarity	NPC477042
0.7801	Intermediate Similarity	NPC73994
0.7795	Intermediate Similarity	NPC321708
0.7789	Intermediate Similarity	NPC240088
0.7789	Intermediate Similarity	NPC473380
0.7788	Intermediate Similarity	NPC477979
0.7784	Intermediate Similarity	NPC478184
0.7778	Intermediate Similarity	NPC293216
0.7767	Intermediate Similarity	NPC123839
0.7766	Intermediate Similarity	NPC47190
0.7754	Intermediate Similarity	NPC70949
0.775	Intermediate Similarity	NPC131887
0.7742	Intermediate Similarity	NPC267078
0.7742	Intermediate Similarity	NPC935
0.7722	Intermediate Similarity	NPC321911
0.7717	Intermediate Similarity	NPC474492
0.7717	Intermediate Similarity	NPC293487
0.7706	Intermediate Similarity	NPC474357
0.7701	Intermediate Similarity	NPC114637
0.7692	Intermediate Similarity	NPC118940
0.7692	Intermediate Similarity	NPC62749
0.7688	Intermediate Similarity	NPC271797
0.7688	Intermediate Similarity	NPC21174
0.768	Intermediate Similarity	NPC53947
0.7676	Intermediate Similarity	NPC470680
0.7676	Intermediate Similarity	NPC100104
0.7667	Intermediate Similarity	NPC201380
0.7667	Intermediate Similarity	NPC179787
0.7667	Intermediate Similarity	NPC471192
0.7667	Intermediate Similarity	NPC470732
0.7667	Intermediate Similarity	NPC36405
0.7667	Intermediate Similarity	NPC470731
0.7667	Intermediate Similarity	NPC469811
0.7662	Intermediate Similarity	NPC474916
0.7644	Intermediate Similarity	NPC82370
0.7637	Intermediate Similarity	NPC472260
0.7633	Intermediate Similarity	NPC478158
0.7633	Intermediate Similarity	NPC162860
0.7622	Intermediate Similarity	NPC92796
0.7622	Intermediate Similarity	NPC135141
0.7621	Intermediate Similarity	NPC54420
0.7619	Intermediate Similarity	NPC478157
0.7617	Intermediate Similarity	NPC91179
0.7615	Intermediate Similarity	NPC470323
0.7614	Intermediate Similarity	NPC213629
0.7611	Intermediate Similarity	NPC63545
0.7611	Intermediate Similarity	NPC288838
0.7606	Intermediate Similarity	NPC478183
0.7604	Intermediate Similarity	NPC157583
0.7604	Intermediate Similarity	NPC83774
0.7596	Intermediate Similarity	NPC251391
0.759	Intermediate Similarity	NPC467063
0.7588	Intermediate Similarity	NPC272458
0.758	Intermediate Similarity	NPC200553
0.758	Intermediate Similarity	NPC279189
0.7577	Intermediate Similarity	NPC470677
0.7574	Intermediate Similarity	NPC171317
0.7574	Intermediate Similarity	NPC67288
0.7568	Intermediate Similarity	NPC216643
0.7565	Intermediate Similarity	NPC53534
0.754	Intermediate Similarity	NPC214106
0.754	Intermediate Similarity	NPC478185
0.754	Intermediate Similarity	NPC470203
0.7526	Intermediate Similarity	NPC32534
0.7526	Intermediate Similarity	NPC61011
0.7526	Intermediate Similarity	NPC88110
0.7525	Intermediate Similarity	NPC103119
0.7524	Intermediate Similarity	NPC132539
0.7523	Intermediate Similarity	NPC276657
0.7512	Intermediate Similarity	NPC294693
0.7512	Intermediate Similarity	NPC202812
0.7511	Intermediate Similarity	NPC174489
0.75	Intermediate Similarity	NPC121327
0.75	Intermediate Similarity	NPC122436
0.75	Intermediate Similarity	NPC265100
0.7488	Intermediate Similarity	NPC472064
0.7487	Intermediate Similarity	NPC122141
0.7487	Intermediate Similarity	NPC470204
0.7487	Intermediate Similarity	NPC154339
0.7477	Intermediate Similarity	NPC476491
0.7477	Intermediate Similarity	NPC162002
0.7475	Intermediate Similarity	NPC472293
0.7474	Intermediate Similarity	NPC12649
0.7473	Intermediate Similarity	NPC236711
0.7463	Intermediate Similarity	NPC247735
0.7463	Intermediate Similarity	NPC267343
0.7463	Intermediate Similarity	NPC81802
0.7463	Intermediate Similarity	NPC472295
0.7463	Intermediate Similarity	NPC472210
0.7463	Intermediate Similarity	NPC269886
0.7459	Intermediate Similarity	NPC470440
0.7459	Intermediate Similarity	NPC467188
0.7456	Intermediate Similarity	NPC63971
0.7456	Intermediate Similarity	NPC91868
0.7447	Intermediate Similarity	NPC242116
0.7445	Intermediate Similarity	NPC178858
0.7444	Intermediate Similarity	NPC26641
0.7441	Intermediate Similarity	NPC110182
0.7441	Intermediate Similarity	NPC477413
0.7441	Intermediate Similarity	NPC75634
0.744	Intermediate Similarity	NPC473376
0.7435	Intermediate Similarity	NPC91895
0.7433	Intermediate Similarity	NPC80681
0.7432	Intermediate Similarity	NPC123906
0.743	Intermediate Similarity	NPC281049
0.7427	Intermediate Similarity	NPC143977
0.7427	Intermediate Similarity	NPC476073
0.7427	Intermediate Similarity	NPC57398
0.7424	Intermediate Similarity	NPC476527
0.7423	Intermediate Similarity	NPC237188
0.7423	Intermediate Similarity	NPC84827
0.7423	Intermediate Similarity	NPC59269
0.7423	Intermediate Similarity	NPC145885
0.7423	Intermediate Similarity	NPC14113
0.7421	Intermediate Similarity	NPC196718
0.7419	Intermediate Similarity	NPC476817
0.7413	Intermediate Similarity	NPC472292
0.7411	Intermediate Similarity	NPC46895
0.7406	Intermediate Similarity	NPC234078
0.7406	Intermediate Similarity	NPC221100
0.7402	Intermediate Similarity	NPC34837
0.7402	Intermediate Similarity	NPC474389

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 NPC317701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	659
0.2-0.3	1013
0.3-0.4	2244
0.4-0.5	2052
0.5-0.6	1832
0.6-0.7	866
0.7-0.8	174
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8418	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD2443	Approved
0.8291	Intermediate Similarity	NPD2442	Approved
0.8283	Intermediate Similarity	NPD2008	Discontinued
0.8272	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD4922	Phase 2
0.8218	Intermediate Similarity	NPD2411	Approved
0.8144	Intermediate Similarity	NPD7619	Phase 3
0.8144	Intermediate Similarity	NPD7618	Phase 3
0.8069	Intermediate Similarity	NPD2408	Discontinued
0.8053	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD6459	Phase 2
0.801	Intermediate Similarity	NPD4848	Phase 1
0.799	Intermediate Similarity	NPD5017	Discontinued
0.7981	Intermediate Similarity	NPD5199	Approved
0.7981	Intermediate Similarity	NPD5198	Approved
0.7958	Intermediate Similarity	NPD7564	Discontinued
0.7895	Intermediate Similarity	NPD2479	Phase 3
0.7895	Intermediate Similarity	NPD2481	Approved
0.7892	Intermediate Similarity	NPD1600	Suspended
0.7882	Intermediate Similarity	NPD3905	Phase 3
0.7876	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7837	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6787	Phase 2
0.7794	Intermediate Similarity	NPD1506	Discontinued
0.7789	Intermediate Similarity	NPD2880	Discontinued
0.7789	Intermediate Similarity	NPD6664	Approved
0.7772	Intermediate Similarity	NPD2879	Approved
0.7772	Intermediate Similarity	NPD2881	Approved
0.772	Intermediate Similarity	NPD3318	Approved
0.772	Intermediate Similarity	NPD3319	Phase 1
0.772	Intermediate Similarity	NPD3320	Approved
0.7718	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD5426	Phase 3
0.7681	Intermediate Similarity	NPD4051	Discontinued
0.7681	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD6470	Phase 3
0.7673	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2509	Approved
0.767	Intermediate Similarity	NPD2510	Approved
0.7653	Intermediate Similarity	NPD4988	Discontinued
0.7644	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4075	Phase 2
0.755	Intermediate Similarity	NPD460	Discontinued
0.7547	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD1658	Discontinued
0.7537	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6999	Discontinued
0.7536	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5473	Discontinued
0.7512	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3583	Phase 2
0.75	Intermediate Similarity	NPD7666	Phase 3
0.75	Intermediate Similarity	NPD7665	Phase 2
0.75	Intermediate Similarity	NPD4883	Approved
0.7487	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD4863	Approved
0.7474	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6210	Phase 3
0.7441	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD6954	Phase 2
0.7436	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6217	Discontinued
0.7419	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3389	Approved
0.7418	Intermediate Similarity	NPD3394	Approved
0.7418	Intermediate Similarity	NPD3393	Approved
0.7397	Intermediate Similarity	NPD6164	Phase 2
0.7397	Intermediate Similarity	NPD6165	Phase 2
0.7393	Intermediate Similarity	NPD6152	Phase 1
0.7393	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3961	Discontinued
0.7374	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5854	Approved
0.7363	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7656	Approved
0.7358	Intermediate Similarity	NPD7657	Approved
0.7356	Intermediate Similarity	NPD5901	Discontinued
0.7353	Intermediate Similarity	NPD5446	Phase 2
0.7347	Intermediate Similarity	NPD6595	Phase 3
0.7337	Intermediate Similarity	NPD5809	Phase 3
0.7337	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7026	Phase 2
0.7317	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1982	Phase 1
0.7313	Intermediate Similarity	NPD5686	Approved
0.7313	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5685	Approved
0.7309	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3078	Approved
0.7296	Intermediate Similarity	NPD3077	Approved
0.7296	Intermediate Similarity	NPD3076	Approved
0.7296	Intermediate Similarity	NPD3079	Approved
0.7295	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1722	Approved
0.7292	Intermediate Similarity	NPD1343	Approved
0.7291	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7781	Approved
0.7285	Intermediate Similarity	NPD7780	Approved
0.7282	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7603	Discontinued
0.7268	Intermediate Similarity	NPD1952	Discontinued
0.7264	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6771	Discontinued
0.726	Intermediate Similarity	NPD6173	Approved
0.726	Intermediate Similarity	NPD7187	Phase 2
0.7255	Intermediate Similarity	NPD7944	Discontinued
0.7231	Intermediate Similarity	NPD482	Approved
0.723	Intermediate Similarity	NPD7470	Discontinued
0.7229	Intermediate Similarity	NPD4558	Phase 2
0.7225	Intermediate Similarity	NPD6176	Phase 1
0.722	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2837	Discontinued
0.7214	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7817	Phase 1
0.7212	Intermediate Similarity	NPD7727	Phase 2
0.7208	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7887	Approved
0.7207	Intermediate Similarity	NPD7888	Approved
0.7204	Intermediate Similarity	NPD8322	Phase 2
0.7204	Intermediate Similarity	NPD3839	Phase 2
0.7204	Intermediate Similarity	NPD3840	Phase 2
0.7204	Intermediate Similarity	NPD2172	Phase 1
0.7198	Intermediate Similarity	NPD2405	Phase 3
0.7196	Intermediate Similarity	NPD7454	Approved
0.7196	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8093	Discontinued
0.7196	Intermediate Similarity	NPD7455	Approved
0.7195	Intermediate Similarity	NPD8289	Discontinued
0.7195	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7209	Approved
0.719	Intermediate Similarity	NPD8115	Approved
0.719	Intermediate Similarity	NPD8114	Approved
0.719	Intermediate Similarity	NPD3947	Discontinued
0.719	Intermediate Similarity	NPD7207	Approved
0.719	Intermediate Similarity	NPD6987	Phase 1
0.719	Intermediate Similarity	NPD7208	Approved
0.7189	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD1270	Approved
0.7186	Intermediate Similarity	NPD2092	Phase 2
0.7186	Intermediate Similarity	NPD2095	Phase 2
0.7186	Intermediate Similarity	NPD2094	Phase 2
0.7182	Intermediate Similarity	NPD786	Approved
0.7178	Intermediate Similarity	NPD7175	Phase 1
0.7174	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5400	Approved
0.7172	Intermediate Similarity	NPD3927	Phase 2
0.7171	Intermediate Similarity	NPD5855	Phase 3
0.7171	Intermediate Similarity	NPD5853	Phase 3
0.717	Intermediate Similarity	NPD5421	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6986	Phase 1
0.7157	Intermediate Similarity	NPD4181	Approved
0.7157	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7791	Approved
0.7156	Intermediate Similarity	NPD7001	Phase 3
0.7156	Intermediate Similarity	NPD7952	Approved
0.7156	Intermediate Similarity	NPD7950	Approved
0.7156	Intermediate Similarity	NPD7953	Approved
0.7156	Intermediate Similarity	NPD7789	Approved
0.7156	Intermediate Similarity	NPD7951	Approved
0.7156	Intermediate Similarity	NPD7790	Approved
0.7156	Intermediate Similarity	NPD3967	Approved
0.715	Intermediate Similarity	NPD2096	Phase 2
0.715	Intermediate Similarity	NPD2091	Phase 2
0.715	Intermediate Similarity	NPD6178	Phase 3
0.7143	Intermediate Similarity	NPD5643	Phase 2
0.7136	Intermediate Similarity	NPD1895	Discontinued
0.7136	Intermediate Similarity	NPD6226	Phase 3
0.7135	Intermediate Similarity	NPD3323	Discontinued
0.713	Intermediate Similarity	NPD7970	Approved
0.713	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6837	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6579	Phase 2
0.7111	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4299	Phase 1
0.7092	Intermediate Similarity	NPD4524	Discontinued
0.7092	Intermediate Similarity	NPD3868	Phase 1
0.7089	Intermediate Similarity	NPD7191	Phase 2
0.7085	Intermediate Similarity	NPD7730	Approved
0.7085	Intermediate Similarity	NPD7731	Approved
0.7083	Intermediate Similarity	NPD5888	Phase 2
0.7083	Intermediate Similarity	NPD8094	Discontinued
0.7083	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3431	Approved
0.7073	Intermediate Similarity	NPD3430	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