NPASS Compound

Structure

CID76079 OpenBabel06191715412D 26 31 0 0 1 0 0 0 0 0999 V2000 -5.2812 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 4.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6231 4.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0243 3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 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 -5.2812 1.8090 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 -4.4152 3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 -4.4152 1.3090 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 -5.2812 2.8090 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.4152 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 6 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 23 1 0 0 0 0 7 13 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 9 21 1 0 0 0 0 10 19 2 0 0 0 0 10 22 1 0 0 0 0 11 20 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 12 26 1 0 0 0 0 13 23 1 6 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	347.15
Volume:	356.642
LogP:	5.243
LogD:	3.403
LogS:	-6.814
# Rotatable Bonds:	1
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	3.028
Fsp3:	0.364
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:	-5.231
MDCK Permeability:	3.4394652175251395e-05
Pgp-inhibitor:	0.742
Pgp-substrate:	0.923
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927
Plasma Protein Binding (PPB):	91.15101623535156%
Volume Distribution (VD):	2.237
Pgp-substrate:	2.0048727989196777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.885
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.603
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.991
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	14.846
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.943
Rat Oral Acute Toxicity:	0.554
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.947
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC76079

Natural Product ID:	NPC76079
*Common Name:**	SQVBRXGPXHOUAI-CYBMUJFWSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Ficuseptine C
Standard InCHIKey:	SQVBRXGPXHOUAI-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C22H21NO3/c1-24-14-4-5-15-17(8-14)19-10-22-21(25-12-26-22)9-18(19)16-7-13-3-2-6-23(13)11-20(15)16/h4-5,8-10,13H,2-3,6-7,11-12H2,1H3/t13-/m1/s1
SMILES:	COc1ccc2c(c1)c1cc3OCOc3cc1c1c2CN2CCC[C@@H]2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255848
PubChem CID:	11359996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24897106]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24981	Dimetia capitellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18056	Silene rubicunda	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18788	Isertia hypoleuca	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18515	Uncaria pilosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14290	Bryonia cretica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17803	Parmelia omphalodes	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24981	Dimetia capitellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28410	Nandina domestica	Species	Berberidaceae	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
GI50	3
IC50	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	=	323.0	nM	PMID[534671]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	=	156.0	nM	PMID[534671]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	371.0	nM	PMID[534671]
NPT2	Others	Unspecified		IC50	=	1244.0	nM	PMID[534671]
NPT2	Others	Unspecified		IC50	=	2566.0	nM	PMID[534671]
NPT2	Others	Unspecified		IC50	=	3383.0	nM	PMID[534671]
NPT2	Others	Unspecified		IC50	=	2440.0	nM	PMID[534671]

☑ 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 NPC76079 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	355
0.1-0.2	1628
0.2-0.3	7609
0.3-0.4	10295
0.4-0.5	7886
0.5-0.6	11590
0.6-0.7	2536
0.7-0.8	662
0.8-0.85	98
0.85-0.9	30
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9517	High Similarity	NPC95075
0.9517	High Similarity	NPC253883
0.9517	High Similarity	NPC90844
0.9388	High Similarity	NPC219162
0.92	High Similarity	NPC26601
0.9189	High Similarity	NPC130941
0.915	High Similarity	NPC477080
0.9122	High Similarity	NPC144863
0.9091	High Similarity	NPC160298
0.9091	High Similarity	NPC232924
0.9091	High Similarity	NPC477559
0.9091	High Similarity	NPC306902
0.9091	High Similarity	NPC266753
0.9	High Similarity	NPC92541
0.8954	High Similarity	NPC244112
0.8947	High Similarity	NPC210148
0.8947	High Similarity	NPC233029
0.8933	High Similarity	NPC475959
0.8924	High Similarity	NPC210918
0.8917	High Similarity	NPC225774
0.8861	High Similarity	NPC476432
0.8861	High Similarity	NPC24264
0.8861	High Similarity	NPC219341
0.8859	High Similarity	NPC145304
0.8805	High Similarity	NPC298979
0.8805	High Similarity	NPC247389
0.8797	High Similarity	NPC167546
0.8797	High Similarity	NPC16805
0.8797	High Similarity	NPC302527
0.8774	High Similarity	NPC186063
0.8774	High Similarity	NPC234392
0.8774	High Similarity	NPC31311
0.875	High Similarity	NPC241055
0.8742	High Similarity	NPC86144
0.8742	High Similarity	NPC304659
0.8734	High Similarity	NPC233650
0.871	High Similarity	NPC78733
0.871	High Similarity	NPC216459
0.871	High Similarity	NPC138487
0.871	High Similarity	NPC41178
0.8679	High Similarity	NPC134858
0.8679	High Similarity	NPC168409
0.8654	High Similarity	NPC146288
0.8636	High Similarity	NPC326316
0.8636	High Similarity	NPC81733
0.8627	High Similarity	NPC211296
0.8616	High Similarity	NPC189470
0.8598	High Similarity	NPC287588
0.8571	High Similarity	NPC210140
0.8571	High Similarity	NPC150879
0.8528	High Similarity	NPC19520
0.8528	High Similarity	NPC149090
0.8523	High Similarity	NPC314682
0.8471	Intermediate Similarity	NPC93593
0.8467	Intermediate Similarity	NPC213206
0.8467	Intermediate Similarity	NPC188163
0.8467	Intermediate Similarity	NPC328750
0.8467	Intermediate Similarity	NPC474915
0.8466	Intermediate Similarity	NPC6152
0.8462	Intermediate Similarity	NPC148898
0.8452	Intermediate Similarity	NPC223125
0.8446	Intermediate Similarity	NPC7018
0.8443	Intermediate Similarity	NPC179704
0.8434	Intermediate Similarity	NPC148693
0.8434	Intermediate Similarity	NPC118633
0.8434	Intermediate Similarity	NPC294790
0.8434	Intermediate Similarity	NPC114364
0.8434	Intermediate Similarity	NPC320223
0.8428	Intermediate Similarity	NPC111485
0.8424	Intermediate Similarity	NPC199465
0.8424	Intermediate Similarity	NPC229166
0.8424	Intermediate Similarity	NPC128560
0.8387	Intermediate Similarity	NPC44869
0.8383	Intermediate Similarity	NPC126284
0.8375	Intermediate Similarity	NPC215829
0.8375	Intermediate Similarity	NPC97072
0.8365	Intermediate Similarity	NPC476572
0.8355	Intermediate Similarity	NPC136860
0.8355	Intermediate Similarity	NPC476567
0.8355	Intermediate Similarity	NPC128019
0.8354	Intermediate Similarity	NPC152212
0.8354	Intermediate Similarity	NPC99659
0.8354	Intermediate Similarity	NPC325871
0.8344	Intermediate Similarity	NPC223124
0.8344	Intermediate Similarity	NPC470925
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC169743
0.8333	Intermediate Similarity	NPC238530
0.8302	Intermediate Similarity	NPC203784
0.8302	Intermediate Similarity	NPC126519
0.8302	Intermediate Similarity	NPC170503
0.8299	Intermediate Similarity	NPC118419
0.8284	Intermediate Similarity	NPC249405
0.8284	Intermediate Similarity	NPC248642
0.8276	Intermediate Similarity	NPC100129
0.8274	Intermediate Similarity	NPC267408
0.8272	Intermediate Similarity	NPC320104
0.8266	Intermediate Similarity	NPC302001
0.8263	Intermediate Similarity	NPC112575
0.8261	Intermediate Similarity	NPC166014
0.8261	Intermediate Similarity	NPC27410
0.8258	Intermediate Similarity	NPC106295
0.8258	Intermediate Similarity	NPC16107
0.8258	Intermediate Similarity	NPC210437
0.8258	Intermediate Similarity	NPC476144
0.8258	Intermediate Similarity	NPC51957
0.8247	Intermediate Similarity	NPC185838
0.8235	Intermediate Similarity	NPC156576
0.8232	Intermediate Similarity	NPC57812
0.8232	Intermediate Similarity	NPC474324
0.8225	Intermediate Similarity	NPC32413
0.8225	Intermediate Similarity	NPC474506
0.8221	Intermediate Similarity	NPC247972
0.8214	Intermediate Similarity	NPC23219
0.821	Intermediate Similarity	NPC60186
0.8205	Intermediate Similarity	NPC7467
0.8204	Intermediate Similarity	NPC477558
0.8198	Intermediate Similarity	NPC474904
0.8182	Intermediate Similarity	NPC266176
0.8182	Intermediate Similarity	NPC82533
0.8182	Intermediate Similarity	NPC475845
0.8182	Intermediate Similarity	NPC158148
0.8182	Intermediate Similarity	NPC290759
0.8176	Intermediate Similarity	NPC116284
0.8166	Intermediate Similarity	NPC258695
0.8166	Intermediate Similarity	NPC470879
0.8141	Intermediate Similarity	NPC321505
0.8141	Intermediate Similarity	NPC476151
0.8141	Intermediate Similarity	NPC179825
0.8141	Intermediate Similarity	NPC191376
0.8133	Intermediate Similarity	NPC75958
0.8133	Intermediate Similarity	NPC474708
0.8133	Intermediate Similarity	NPC11147
0.8129	Intermediate Similarity	NPC135772
0.8121	Intermediate Similarity	NPC190332
0.8121	Intermediate Similarity	NPC181653
0.8121	Intermediate Similarity	NPC100566
0.8118	Intermediate Similarity	NPC476574
0.8118	Intermediate Similarity	NPC312918
0.8118	Intermediate Similarity	NPC155442
0.8118	Intermediate Similarity	NPC477561
0.8098	Intermediate Similarity	NPC24954
0.8092	Intermediate Similarity	NPC237579
0.8092	Intermediate Similarity	NPC312531
0.8089	Intermediate Similarity	NPC135538
0.8089	Intermediate Similarity	NPC246587
0.8089	Intermediate Similarity	NPC428
0.8089	Intermediate Similarity	NPC24233
0.8089	Intermediate Similarity	NPC476571
0.8089	Intermediate Similarity	NPC147390
0.8086	Intermediate Similarity	NPC106786
0.8084	Intermediate Similarity	NPC470739
0.8084	Intermediate Similarity	NPC225597
0.8084	Intermediate Similarity	NPC65403
0.8084	Intermediate Similarity	NPC477640
0.8075	Intermediate Similarity	NPC247639
0.8075	Intermediate Similarity	NPC25084
0.8072	Intermediate Similarity	NPC58766
0.8072	Intermediate Similarity	NPC475686
0.807	Intermediate Similarity	NPC275132
0.8068	Intermediate Similarity	NPC162653
0.8049	Intermediate Similarity	NPC59567
0.8049	Intermediate Similarity	NPC324144
0.8041	Intermediate Similarity	NPC160193
0.8038	Intermediate Similarity	NPC103379
0.8038	Intermediate Similarity	NPC477565
0.8036	Intermediate Similarity	NPC2314
0.8035	Intermediate Similarity	NPC214116
0.8027	Intermediate Similarity	NPC177167
0.8026	Intermediate Similarity	NPC193528
0.8024	Intermediate Similarity	NPC311991
0.8024	Intermediate Similarity	NPC474475
0.8013	Intermediate Similarity	NPC130926
0.8012	Intermediate Similarity	NPC12053
0.8012	Intermediate Similarity	NPC123323
0.8012	Intermediate Similarity	NPC474931
0.8012	Intermediate Similarity	NPC117188
0.8012	Intermediate Similarity	NPC205421
0.8012	Intermediate Similarity	NPC145832
0.8012	Intermediate Similarity	NPC158376
0.8012	Intermediate Similarity	NPC306555
0.8012	Intermediate Similarity	NPC81218
0.8	Intermediate Similarity	NPC253043
0.8	Intermediate Similarity	NPC477563
0.8	Intermediate Similarity	NPC212794
0.8	Intermediate Similarity	NPC306843
0.8	Intermediate Similarity	NPC196447
0.8	Intermediate Similarity	NPC136508
0.8	Intermediate Similarity	NPC13504
0.8	Intermediate Similarity	NPC96603
0.8	Intermediate Similarity	NPC78222
0.8	Intermediate Similarity	NPC231198
0.7988	Intermediate Similarity	NPC304675
0.7987	Intermediate Similarity	NPC88249
0.7987	Intermediate Similarity	NPC97221
0.7987	Intermediate Similarity	NPC220858
0.7987	Intermediate Similarity	NPC192768
0.7987	Intermediate Similarity	NPC151895
0.7978	Intermediate Similarity	NPC193906

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 NPC76079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	768
0.2-0.3	905
0.3-0.4	1929
0.4-0.5	2915
0.5-0.6	1790
0.6-0.7	530
0.7-0.8	93
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD5084	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD4584	Approved
0.8247	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4017	Approved
0.7881	Intermediate Similarity	NPD3109	Approved
0.7881	Intermediate Similarity	NPD3110	Approved
0.7791	Intermediate Similarity	NPD7298	Approved
0.7748	Intermediate Similarity	NPD5718	Phase 2
0.7748	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7831	Phase 2
0.7711	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7833	Phase 2
0.7702	Intermediate Similarity	NPD6030	Approved
0.7702	Intermediate Similarity	NPD6031	Approved
0.7702	Intermediate Similarity	NPD3641	Approved
0.7702	Intermediate Similarity	NPD3640	Phase 3
0.7702	Intermediate Similarity	NPD3639	Approved
0.7702	Intermediate Similarity	NPD4727	Phase 1
0.7697	Intermediate Similarity	NPD4474	Approved
0.7697	Intermediate Similarity	NPD4475	Approved
0.7682	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7400	Phase 3
0.7662	Intermediate Similarity	NPD2492	Phase 1
0.7651	Intermediate Similarity	NPD6788	Approved
0.7625	Intermediate Similarity	NPD2420	Approved
0.7625	Intermediate Similarity	NPD2421	Approved
0.761	Intermediate Similarity	NPD5241	Discontinued
0.759	Intermediate Similarity	NPD5977	Approved
0.759	Intermediate Similarity	NPD5978	Approved
0.7582	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7802	Discontinued
0.7558	Intermediate Similarity	NPD8099	Discontinued
0.7558	Intermediate Similarity	NPD8252	Approved
0.7558	Intermediate Similarity	NPD8251	Approved
0.7529	Intermediate Similarity	NPD3051	Approved
0.7516	Intermediate Similarity	NPD7598	Phase 2
0.7515	Intermediate Similarity	NPD4772	Phase 2
0.7515	Intermediate Similarity	NPD4773	Phase 2
0.7514	Intermediate Similarity	NPD8156	Discontinued
0.75	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7281	Phase 3
0.75	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD5604	Discontinued
0.747	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3845	Phase 1
0.7442	Intermediate Similarity	NPD4481	Phase 3
0.7442	Intermediate Similarity	NPD2898	Approved
0.744	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4166	Phase 2
0.7421	Intermediate Similarity	NPD7037	Approved
0.7407	Intermediate Similarity	NPD4859	Phase 1
0.7407	Intermediate Similarity	NPD3124	Discontinued
0.7394	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4420	Approved
0.7391	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6896	Approved
0.7389	Intermediate Similarity	NPD6895	Approved
0.7384	Intermediate Similarity	NPD2969	Approved
0.7384	Intermediate Similarity	NPD2970	Approved
0.7378	Intermediate Similarity	NPD5976	Discontinued
0.7368	Intermediate Similarity	NPD7247	Discontinued
0.7351	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4108	Discontinued
0.7341	Intermediate Similarity	NPD2489	Approved
0.7341	Intermediate Similarity	NPD27	Approved
0.7329	Intermediate Similarity	NPD6748	Discontinued
0.7326	Intermediate Similarity	NPD4010	Discontinued
0.7299	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7294	Phase 1
0.7285	Intermediate Similarity	NPD1669	Approved
0.7283	Intermediate Similarity	NPD5582	Discontinued
0.7267	Intermediate Similarity	NPD6107	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7267	Intermediate Similarity	NPD4237	Approved
0.7263	Intermediate Similarity	NPD8054	Approved
0.7263	Intermediate Similarity	NPD8053	Approved
0.7238	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5005	Approved
0.7234	Intermediate Similarity	NPD5006	Approved
0.7225	Intermediate Similarity	NPD6071	Discontinued
0.7222	Intermediate Similarity	NPD5754	Discontinued
0.7219	Intermediate Similarity	NPD2977	Approved
0.7219	Intermediate Similarity	NPD2978	Approved
0.7208	Intermediate Similarity	NPD3763	Approved
0.7205	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2560	Approved
0.7176	Intermediate Similarity	NPD2563	Approved
0.7169	Intermediate Similarity	NPD1914	Approved
0.7167	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5177	Phase 3
0.7143	Intermediate Similarity	NPD7291	Discontinued
0.7135	Intermediate Similarity	NPD6297	Approved
0.7134	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6331	Phase 2
0.7115	Intermediate Similarity	NPD5155	Approved
0.7115	Intermediate Similarity	NPD5156	Approved
0.7111	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2968	Approved
0.7111	Intermediate Similarity	NPD2971	Approved
0.7101	Intermediate Similarity	NPD7110	Phase 1
0.7101	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6687	Approved
0.7086	Intermediate Similarity	NPD6688	Approved
0.7083	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3301	Approved
0.7066	Intermediate Similarity	NPD7427	Discontinued
0.7063	Intermediate Similarity	NPD7119	Phase 2
0.7056	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2606	Approved
0.7051	Intermediate Similarity	NPD2605	Approved
0.7051	Intermediate Similarity	NPD3594	Approved
0.7051	Intermediate Similarity	NPD3595	Approved
0.7049	Intermediate Similarity	NPD3349	Phase 2
0.7049	Intermediate Similarity	NPD7906	Approved
0.7048	Intermediate Similarity	NPD7019	Approved
0.7048	Intermediate Similarity	NPD7020	Approved
0.7045	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3705	Approved
0.7035	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7018	Phase 2
0.703	Intermediate Similarity	NPD7124	Phase 2
0.7029	Intermediate Similarity	NPD6747	Phase 1
0.7024	Intermediate Similarity	NPD4210	Discontinued
0.7022	Intermediate Similarity	NPD5313	Approved
0.7022	Intermediate Similarity	NPD5312	Approved
0.702	Intermediate Similarity	NPD2668	Approved
0.702	Intermediate Similarity	NPD2667	Approved
0.7017	Intermediate Similarity	NPD4577	Approved
0.7017	Intermediate Similarity	NPD4578	Approved
0.7012	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7006	Intermediate Similarity	NPD6090	Discontinued
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6873	Phase 2
0.7	Intermediate Similarity	NPD7438	Suspended
0.6994	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3637	Approved
0.6987	Remote Similarity	NPD3635	Approved
0.6987	Remote Similarity	NPD3636	Approved
0.6983	Remote Similarity	NPD3885	Approved
0.6978	Remote Similarity	NPD6853	Approved
0.6978	Remote Similarity	NPD6851	Approved
0.6964	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5720	Discontinued
0.6957	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4093	Discontinued
0.6949	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1421	Approved
0.6948	Remote Similarity	NPD1420	Approved
0.6946	Remote Similarity	NPD1424	Approved
0.6946	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2120	Phase 2
0.6923	Remote Similarity	NPD7313	Approved
0.6923	Remote Similarity	NPD7311	Approved
0.6923	Remote Similarity	NPD7310	Approved
0.6923	Remote Similarity	NPD7905	Discontinued
0.6923	Remote Similarity	NPD7312	Approved
0.6919	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3532	Approved
0.6918	Remote Similarity	NPD3531	Approved
0.6918	Remote Similarity	NPD2674	Phase 3
0.6918	Remote Similarity	NPD3530	Approved
0.691	Remote Similarity	NPD5938	Phase 3
0.6909	Remote Similarity	NPD7466	Approved
0.6905	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3816	Phase 1
0.6904	Remote Similarity	NPD3815	Phase 1
0.6902	Remote Similarity	NPD4663	Approved
0.6897	Remote Similarity	NPD4055	Discovery
0.6889	Remote Similarity	NPD7479	Phase 2
0.6889	Remote Similarity	NPD3920	Phase 2
0.6885	Remote Similarity	NPD7309	Approved
0.6883	Remote Similarity	NPD2232	Approved
0.6883	Remote Similarity	NPD2233	Approved
0.6883	Remote Similarity	NPD2230	Approved
0.6882	Remote Similarity	NPD2488	Approved
0.6882	Remote Similarity	NPD2490	Approved
0.6879	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5160	Discontinued
0.6862	Remote Similarity	NPD6493	Phase 3
0.686	Remote Similarity	NPD7248	Discontinued
0.686	Remote Similarity	NPD3382	Approved
0.686	Remote Similarity	NPD3383	Approved
0.686	Remote Similarity	NPD3384	Approved
0.6859	Remote Similarity	NPD4098	Discontinued
0.6857	Remote Similarity	NPD5709	Phase 3
0.6855	Remote Similarity	NPD5109	Approved
0.6855	Remote Similarity	NPD5110	Phase 2
0.6855	Remote Similarity	NPD5111	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