NPASS Compound

Structure

NPC476331 OpenBabel07101719132D 24 27 0 0 1 0 0 0 0 0999 V2000 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3585 -3.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1421 -1.7695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 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 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3766 -2.0438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 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 -2.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6849 -1.6163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1579 -2.1547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2721 -3.0383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 24 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 21 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 18 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.97
Volume:	348.411
LogP:	2.764
LogD:	2.905
LogS:	-3.249
# Rotatable Bonds:	1
TPSA:	52.93
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	4.576
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	1.7966764062293805e-05
Pgp-inhibitor:	0.058
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.356
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998
Plasma Protein Binding (PPB):	79.2559585571289%
Volume Distribution (VD):	2.582
Pgp-substrate:	14.112631797790527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.704
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.721
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	3.112
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.41
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.783
Carcinogencity:	0.882
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC476331

Natural Product ID:	NPC476331
*Common Name:**	Saldedine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JUGNWQJYSAIQSO-KIAYWQFFSA-N
Standard InCHI:	InChI=1S/C18H19Br2NO3/c1-21-4-3-9-5-13(24-2)17(23)15-14(9)12(21)8-18(15)6-10(19)16(22)11(20)7-18/h5-7,12,16,22-23H,3-4,8H2,1-2H3/t12-,16?,18?/m0/s1
SMILES:	COc1cc2CCN([C@@H]3c2c(c1O)C1(C=C(Br)C(C(=C1)Br)O)C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL565226
PubChem CID:	45271387
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002660] Proaporphines

*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
NPO33411	madagascan tunicate	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19216520]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	10.9	uM	PMID[533876]

☑ 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 NPC476331 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	311
0.1-0.2	1610
0.2-0.3	6595
0.3-0.4	11829
0.4-0.5	7808
0.5-0.6	11531
0.6-0.7	2375
0.7-0.8	527
0.8-0.85	105
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC21885
0.9024	High Similarity	NPC470324
0.882	High Similarity	NPC147091
0.8598	High Similarity	NPC118804
0.8545	High Similarity	NPC249274
0.8545	High Similarity	NPC205167
0.8519	High Similarity	NPC82285
0.8519	High Similarity	NPC133011
0.8447	Intermediate Similarity	NPC103379
0.8447	Intermediate Similarity	NPC477565
0.8438	Intermediate Similarity	NPC321505
0.8438	Intermediate Similarity	NPC179825
0.8438	Intermediate Similarity	NPC191376
0.8395	Intermediate Similarity	NPC274026
0.8385	Intermediate Similarity	NPC428
0.8385	Intermediate Similarity	NPC24233
0.8385	Intermediate Similarity	NPC135538
0.8385	Intermediate Similarity	NPC147390
0.8385	Intermediate Similarity	NPC476571
0.8385	Intermediate Similarity	NPC246587
0.8343	Intermediate Similarity	NPC124657
0.8323	Intermediate Similarity	NPC476151
0.8323	Intermediate Similarity	NPC166014
0.8323	Intermediate Similarity	NPC27410
0.8313	Intermediate Similarity	NPC185838
0.8303	Intermediate Similarity	NPC193949
0.8303	Intermediate Similarity	NPC207757
0.8303	Intermediate Similarity	NPC278799
0.8303	Intermediate Similarity	NPC5238
0.8303	Intermediate Similarity	NPC39701
0.8303	Intermediate Similarity	NPC172765
0.8303	Intermediate Similarity	NPC469817
0.8303	Intermediate Similarity	NPC110416
0.8303	Intermediate Similarity	NPC189266
0.8303	Intermediate Similarity	NPC54379
0.8303	Intermediate Similarity	NPC2413
0.8303	Intermediate Similarity	NPC204828
0.8303	Intermediate Similarity	NPC127674
0.8303	Intermediate Similarity	NPC184026
0.8303	Intermediate Similarity	NPC249797
0.8303	Intermediate Similarity	NPC295691
0.8303	Intermediate Similarity	NPC276588
0.8284	Intermediate Similarity	NPC2770
0.8284	Intermediate Similarity	NPC39103
0.8282	Intermediate Similarity	NPC151895
0.8282	Intermediate Similarity	NPC220858
0.8282	Intermediate Similarity	NPC88249
0.8282	Intermediate Similarity	NPC192768
0.8282	Intermediate Similarity	NPC97221
0.8225	Intermediate Similarity	NPC324144
0.8214	Intermediate Similarity	NPC97072
0.8214	Intermediate Similarity	NPC215829
0.8214	Intermediate Similarity	NPC18402
0.8187	Intermediate Similarity	NPC210140
0.8176	Intermediate Similarity	NPC212794
0.8176	Intermediate Similarity	NPC136508
0.8176	Intermediate Similarity	NPC96603
0.8176	Intermediate Similarity	NPC13504
0.8176	Intermediate Similarity	NPC477563
0.8176	Intermediate Similarity	NPC306843
0.8176	Intermediate Similarity	NPC253043
0.8176	Intermediate Similarity	NPC196447
0.8176	Intermediate Similarity	NPC78222
0.8153	Intermediate Similarity	NPC131204
0.8153	Intermediate Similarity	NPC301050
0.8133	Intermediate Similarity	NPC2295
0.8133	Intermediate Similarity	NPC477564
0.8121	Intermediate Similarity	NPC277669
0.8121	Intermediate Similarity	NPC76213
0.8095	Intermediate Similarity	NPC475326
0.8086	Intermediate Similarity	NPC130926
0.8081	Intermediate Similarity	NPC145832
0.8081	Intermediate Similarity	NPC158376
0.8081	Intermediate Similarity	NPC117188
0.8081	Intermediate Similarity	NPC474931
0.8081	Intermediate Similarity	NPC81218
0.8081	Intermediate Similarity	NPC306555
0.8081	Intermediate Similarity	NPC12053
0.8081	Intermediate Similarity	NPC205421
0.8072	Intermediate Similarity	NPC37272
0.807	Intermediate Similarity	NPC276944
0.807	Intermediate Similarity	NPC232514
0.807	Intermediate Similarity	NPC238530
0.807	Intermediate Similarity	NPC134858
0.8047	Intermediate Similarity	NPC59028
0.8047	Intermediate Similarity	NPC92191
0.8047	Intermediate Similarity	NPC111485
0.8036	Intermediate Similarity	NPC186063
0.8025	Intermediate Similarity	NPC294249
0.8023	Intermediate Similarity	NPC35627
0.8023	Intermediate Similarity	NPC476573
0.8023	Intermediate Similarity	NPC81247
0.8012	Intermediate Similarity	NPC1229
0.8012	Intermediate Similarity	NPC233650
0.8	Intermediate Similarity	NPC314682
0.8	Intermediate Similarity	NPC60538
0.8	Intermediate Similarity	NPC207824
0.7988	Intermediate Similarity	NPC315707
0.7988	Intermediate Similarity	NPC40389
0.7988	Intermediate Similarity	NPC148014
0.7988	Intermediate Similarity	NPC65490
0.7988	Intermediate Similarity	NPC78359
0.7977	Intermediate Similarity	NPC190332
0.7977	Intermediate Similarity	NPC181653
0.7977	Intermediate Similarity	NPC100566
0.7977	Intermediate Similarity	NPC298979
0.7976	Intermediate Similarity	NPC78733
0.7965	Intermediate Similarity	NPC255607
0.7965	Intermediate Similarity	NPC24465
0.7965	Intermediate Similarity	NPC3375
0.7955	Intermediate Similarity	NPC229166
0.7955	Intermediate Similarity	NPC128560
0.7955	Intermediate Similarity	NPC199465
0.7953	Intermediate Similarity	NPC60186
0.795	Intermediate Similarity	NPC328750
0.795	Intermediate Similarity	NPC474915
0.795	Intermediate Similarity	NPC213206
0.795	Intermediate Similarity	NPC188163
0.7943	Intermediate Similarity	NPC225597
0.7943	Intermediate Similarity	NPC477640
0.7943	Intermediate Similarity	NPC470739
0.7943	Intermediate Similarity	NPC239775
0.7931	Intermediate Similarity	NPC290759
0.7931	Intermediate Similarity	NPC475686
0.7931	Intermediate Similarity	NPC158148
0.7931	Intermediate Similarity	NPC266176
0.7931	Intermediate Similarity	NPC82533
0.7931	Intermediate Similarity	NPC58766
0.7929	Intermediate Similarity	NPC323443
0.7929	Intermediate Similarity	NPC180756
0.7921	Intermediate Similarity	NPC32154
0.7919	Intermediate Similarity	NPC13916
0.7919	Intermediate Similarity	NPC264850
0.7907	Intermediate Similarity	NPC320104
0.7904	Intermediate Similarity	NPC326316
0.7904	Intermediate Similarity	NPC81733
0.7895	Intermediate Similarity	NPC226428
0.7886	Intermediate Similarity	NPC311991
0.7886	Intermediate Similarity	NPC168753
0.7886	Intermediate Similarity	NPC477562
0.7886	Intermediate Similarity	NPC69712
0.7886	Intermediate Similarity	NPC26240
0.7886	Intermediate Similarity	NPC118274
0.7886	Intermediate Similarity	NPC474475
0.7879	Intermediate Similarity	NPC106295
0.7879	Intermediate Similarity	NPC16107
0.7879	Intermediate Similarity	NPC210437
0.7879	Intermediate Similarity	NPC476144
0.7879	Intermediate Similarity	NPC51957
0.7874	Intermediate Similarity	NPC150879
0.7865	Intermediate Similarity	NPC320223
0.7865	Intermediate Similarity	NPC114364
0.7857	Intermediate Similarity	NPC26601
0.7853	Intermediate Similarity	NPC128019
0.7853	Intermediate Similarity	NPC136860
0.7853	Intermediate Similarity	NPC476567
0.7831	Intermediate Similarity	NPC7467
0.7829	Intermediate Similarity	NPC204908
0.7829	Intermediate Similarity	NPC164429
0.7829	Intermediate Similarity	NPC83198
0.7821	Intermediate Similarity	NPC244554
0.7821	Intermediate Similarity	NPC126284
0.7809	Intermediate Similarity	NPC241704
0.7809	Intermediate Similarity	NPC237044
0.7797	Intermediate Similarity	NPC66341
0.7797	Intermediate Similarity	NPC2314
0.7797	Intermediate Similarity	NPC477020
0.7797	Intermediate Similarity	NPC192135
0.7778	Intermediate Similarity	NPC129603
0.7771	Intermediate Similarity	NPC160193
0.7765	Intermediate Similarity	NPC99659
0.7765	Intermediate Similarity	NPC325871
0.7765	Intermediate Similarity	NPC474325
0.7759	Intermediate Similarity	NPC284183
0.7759	Intermediate Similarity	NPC121275
0.7759	Intermediate Similarity	NPC4138
0.7753	Intermediate Similarity	NPC304675
0.7753	Intermediate Similarity	NPC329969
0.7753	Intermediate Similarity	NPC187678
0.7751	Intermediate Similarity	NPC470924
0.7751	Intermediate Similarity	NPC148898
0.7735	Intermediate Similarity	NPC248642
0.7735	Intermediate Similarity	NPC116284
0.7725	Intermediate Similarity	NPC475959
0.7722	Intermediate Similarity	NPC474745
0.7714	Intermediate Similarity	NPC256012
0.7714	Intermediate Similarity	NPC240841
0.7714	Intermediate Similarity	NPC42549
0.7714	Intermediate Similarity	NPC317272
0.7714	Intermediate Similarity	NPC250846
0.7714	Intermediate Similarity	NPC268503
0.7709	Intermediate Similarity	NPC474470
0.7701	Intermediate Similarity	NPC293871
0.7701	Intermediate Similarity	NPC124433
0.7697	Intermediate Similarity	NPC152680
0.7697	Intermediate Similarity	NPC190783
0.7697	Intermediate Similarity	NPC232386
0.7692	Intermediate Similarity	NPC156576
0.7688	Intermediate Similarity	NPC160298
0.7688	Intermediate Similarity	NPC4304

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 NPC476331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	768
0.2-0.3	1113
0.3-0.4	2587
0.4-0.5	2505
0.5-0.6	1439
0.6-0.7	459
0.7-0.8	74
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD2898	Approved
0.8246	Intermediate Similarity	NPD27	Approved
0.8246	Intermediate Similarity	NPD2489	Approved
0.8235	Intermediate Similarity	NPD4010	Discontinued
0.8081	Intermediate Similarity	NPD2970	Approved
0.8081	Intermediate Similarity	NPD2969	Approved
0.8024	Intermediate Similarity	NPD4772	Phase 2
0.8024	Intermediate Similarity	NPD4773	Phase 2
0.8023	Intermediate Similarity	NPD6071	Discontinued
0.8	Intermediate Similarity	NPD7831	Phase 2
0.8	Intermediate Similarity	NPD7833	Phase 2
0.8	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD2560	Approved
0.7988	Intermediate Similarity	NPD2563	Approved
0.795	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3051	Approved
0.7879	Intermediate Similarity	NPD4584	Approved
0.7771	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5241	Discontinued
0.768	Intermediate Similarity	NPD7310	Approved
0.768	Intermediate Similarity	NPD7313	Approved
0.768	Intermediate Similarity	NPD7311	Approved
0.768	Intermediate Similarity	NPD7312	Approved
0.7637	Intermediate Similarity	NPD7309	Approved
0.7609	Intermediate Similarity	NPD7906	Approved
0.7605	Intermediate Similarity	NPD2420	Approved
0.7605	Intermediate Similarity	NPD2421	Approved
0.7582	Intermediate Similarity	NPD4577	Approved
0.7582	Intermediate Similarity	NPD4578	Approved
0.7574	Intermediate Similarity	NPD3640	Phase 3
0.7574	Intermediate Similarity	NPD3639	Approved
0.7574	Intermediate Similarity	NPD3641	Approved
0.7554	Intermediate Similarity	NPD4663	Approved
0.7514	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4017	Approved
0.7472	Intermediate Similarity	NPD6687	Approved
0.7472	Intermediate Similarity	NPD6688	Approved
0.7446	Intermediate Similarity	NPD8054	Approved
0.7446	Intermediate Similarity	NPD8053	Approved
0.7433	Intermediate Similarity	NPD2490	Approved
0.7433	Intermediate Similarity	NPD2488	Approved
0.743	Intermediate Similarity	NPD4481	Phase 3
0.7401	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5177	Phase 3
0.7356	Intermediate Similarity	NPD7298	Approved
0.7353	Intermediate Similarity	NPD3645	Discontinued
0.734	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3845	Phase 1
0.7301	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3620	Phase 2
0.7267	Intermediate Similarity	NPD6031	Approved
0.7267	Intermediate Similarity	NPD6030	Approved
0.7263	Intermediate Similarity	NPD6107	Approved
0.7239	Intermediate Similarity	NPD2674	Phase 3
0.7229	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4166	Phase 2
0.7126	Intermediate Similarity	NPD1753	Discontinued
0.712	Intermediate Similarity	NPD8156	Discontinued
0.7119	Intermediate Similarity	NPD2978	Approved
0.7119	Intermediate Similarity	NPD2977	Approved
0.7092	Intermediate Similarity	NPD2494	Approved
0.7092	Intermediate Similarity	NPD3450	Approved
0.7092	Intermediate Similarity	NPD2493	Approved
0.7092	Intermediate Similarity	NPD3452	Approved
0.7083	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5978	Approved
0.7079	Intermediate Similarity	NPD5977	Approved
0.7076	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3144	Approved
0.7073	Intermediate Similarity	NPD3145	Approved
0.7073	Intermediate Similarity	NPD5718	Phase 2
0.7065	Intermediate Similarity	NPD8251	Approved
0.7065	Intermediate Similarity	NPD8099	Discontinued
0.7065	Intermediate Similarity	NPD8252	Approved
0.7059	Intermediate Similarity	NPD3060	Approved
0.7056	Intermediate Similarity	NPD2491	Approved
0.7056	Intermediate Similarity	NPD3448	Approved
0.7039	Intermediate Similarity	NPD6788	Approved
0.7027	Intermediate Similarity	NPD5312	Approved
0.7027	Intermediate Similarity	NPD5313	Approved
0.7021	Intermediate Similarity	NPD2971	Approved
0.7021	Intermediate Similarity	NPD2968	Approved
0.7018	Intermediate Similarity	NPD6331	Phase 2
0.7011	Intermediate Similarity	NPD6090	Discontinued
0.6994	Remote Similarity	NPD3124	Discontinued
0.6988	Remote Similarity	NPD3109	Approved
0.6988	Remote Similarity	NPD3110	Approved
0.6985	Remote Similarity	NPD4582	Approved
0.6985	Remote Similarity	NPD4583	Approved
0.6977	Remote Similarity	NPD3692	Discontinued
0.697	Remote Similarity	NPD3057	Approved
0.6964	Remote Similarity	NPD6896	Approved
0.6964	Remote Similarity	NPD6895	Approved
0.6959	Remote Similarity	NPD4236	Phase 3
0.6959	Remote Similarity	NPD3638	Discontinued
0.6959	Remote Similarity	NPD4237	Approved
0.6952	Remote Similarity	NPD6297	Approved
0.6951	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4002	Approved
0.6935	Remote Similarity	NPD4004	Approved
0.6927	Remote Similarity	NPD5772	Approved
0.6927	Remote Similarity	NPD5773	Approved
0.6923	Remote Similarity	NPD2904	Discontinued
0.6919	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD817	Approved
0.6905	Remote Similarity	NPD823	Approved
0.69	Remote Similarity	NPD4040	Phase 1
0.6895	Remote Similarity	NPD6851	Approved
0.6895	Remote Similarity	NPD6853	Approved
0.689	Remote Similarity	NPD3637	Approved
0.689	Remote Similarity	NPD3635	Approved
0.689	Remote Similarity	NPD3636	Approved
0.6888	Remote Similarity	NPD2974	Approved
0.6888	Remote Similarity	NPD2973	Approved
0.6888	Remote Similarity	NPD2975	Approved
0.6886	Remote Similarity	NPD2238	Phase 2
0.6884	Remote Similarity	NPD3533	Approved
0.6884	Remote Similarity	NPD2972	Approved
0.6882	Remote Similarity	NPD2161	Phase 2
0.686	Remote Similarity	NPD4162	Approved
0.6857	Remote Similarity	NPD1424	Approved
0.6857	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4873	Discontinued
0.6842	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4666	Phase 3
0.6831	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4475	Approved
0.6826	Remote Similarity	NPD4474	Approved
0.6818	Remote Similarity	NPD8095	Phase 1
0.6805	Remote Similarity	NPD2157	Approved
0.6798	Remote Similarity	NPD4005	Discontinued
0.6798	Remote Similarity	NPD824	Approved
0.6793	Remote Similarity	NPD7802	Discontinued
0.6789	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4580	Approved
0.6782	Remote Similarity	NPD5160	Discontinued
0.6776	Remote Similarity	NPD5709	Phase 3
0.6761	Remote Similarity	NPD7019	Approved
0.6761	Remote Similarity	NPD7020	Approved
0.6755	Remote Similarity	NPD42	Phase 2
0.6755	Remote Similarity	NPD6042	Phase 2
0.6747	Remote Similarity	NPD2606	Approved
0.6747	Remote Similarity	NPD3594	Approved
0.6747	Remote Similarity	NPD2605	Approved
0.6747	Remote Similarity	NPD3595	Approved
0.6743	Remote Similarity	NPD2120	Phase 2
0.6743	Remote Similarity	NPD6667	Approved
0.6743	Remote Similarity	NPD6666	Approved
0.6731	Remote Similarity	NPD7047	Phase 3
0.6728	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1132	Approved
0.6726	Remote Similarity	NPD1130	Approved
0.6726	Remote Similarity	NPD1136	Approved
0.6722	Remote Similarity	NPD6072	Discontinued
0.6721	Remote Similarity	NPD4055	Discovery
0.672	Remote Similarity	NPD2388	Discontinued
0.6718	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5155	Approved
0.6707	Remote Similarity	NPD5156	Approved
0.6705	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6997	Phase 2
0.6687	Remote Similarity	NPD2232	Approved
0.6687	Remote Similarity	NPD2233	Approved
0.6687	Remote Similarity	NPD2230	Approved
0.6686	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7400	Phase 3
0.6685	Remote Similarity	NPD5976	Discontinued
0.6683	Remote Similarity	NPD4420	Approved
0.6667	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD597	Approved
0.6667	Remote Similarity	NPD3053	Approved
0.6667	Remote Similarity	NPD601	Approved
0.6667	Remote Similarity	NPD3337	Discontinued
0.6667	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD598	Approved
0.6667	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3365	Discontinued
0.6648	Remote Similarity	NPD7124	Phase 2
0.6629	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5754	Discontinued
0.6629	Remote Similarity	NPD7526	Approved
0.6629	Remote Similarity	NPD52	Approved
0.6629	Remote Similarity	NPD6748	Discontinued
0.6628	Remote Similarity	NPD2156	Approved
0.6628	Remote Similarity	NPD2154	Approved
0.6628	Remote Similarity	NPD2155	Approved
0.6627	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5676	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