NPASS Compound

Structure

CID282760 OpenBabel06191716092D 29 29 0 0 1 0 0 0 0 0999 V2000 2.0863 -10.3354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6850 -11.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1419 -6.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3621 -3.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9107 -8.7173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1309 -5.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3511 -3.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5040 -9.6309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3229 -7.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7242 -6.8902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5431 -5.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9444 -4.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7634 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 -1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0918 -10.4399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7297 -6.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9499 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1701 -1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5714 -0.4954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 19 2 0 0 0 0 9 20 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 22 2 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 27 1 0 0 0 0 23 24 1 0 0 0 0 24 15 1 1 0 0 0 24 29 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	451.742
LogP:	5.045
LogD:	4.167
LogS:	-3.938
# Rotatable Bonds:	13
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	3.622
Fsp3:	0.52
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:	-4.91
MDCK Permeability:	1.8216589523945004e-05
Pgp-inhibitor:	0.169
Pgp-substrate:	0.241
Human Intestinal Absorption (HIA):	0.678
20% Bioavailability (F20%):	0.257
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	94.70476531982422%
Volume Distribution (VD):	0.434
Pgp-substrate:	1.565490484237671%

ADMET: Metabolism

CYP1A2-inhibitor:	0.171
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.175
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.753
CYP2D6-substrate:	0.562
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	6.125
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.811
Skin Sensitization:	0.95
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC282760

Natural Product ID:	NPC282760
*Common Name:**	Hippolide E
IUPAC Name:	(2R)-3-(hydroxymethyl)-2-[(2E,6E,10E)-3-(hydroxymethyl)-7,11,15-trimethylhexadeca-2,6,10,14-tetraenyl]-2H-furan-5-one
Synonyms:	Hippolide E
Standard InCHIKey:	ZPTKQNSPWUWKEN-QAXNIAIFSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-19(2)8-5-9-20(3)10-6-11-21(4)12-7-13-22(17-26)14-15-24-23(18-27)16-25(28)29-24/h8,10,12,14,16,24,26-27H,5-7,9,11,13,15,17-18H2,1-4H3/b20-10+,21-12+,22-14+/t24-/m1/s1
SMILES:	CC(=CCC/C(=C/CC/C(=C/CC/C(=CC[C@@H]1C(=CC(=O)O1)CO)/CO)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784623
PubChem CID:	53355992
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO15322	Hippospongia lachne	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548579]
NPO15322	Hippospongia lachne	Species	Spongiidae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	IC50	=	40350.0	nM	PMID[556171]

☑ 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 NPC282760 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	155
0.1-0.2	2452
0.2-0.3	10203
0.3-0.4	17651
0.4-0.5	7333
0.5-0.6	3469
0.6-0.7	1164
0.7-0.8	236
0.8-0.85	28
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC470123
0.8615	High Similarity	NPC146811
0.8529	High Similarity	NPC316185
0.8438	Intermediate Similarity	NPC68110
0.8387	Intermediate Similarity	NPC223679
0.8333	Intermediate Similarity	NPC37382
0.8333	Intermediate Similarity	NPC209135
0.8333	Intermediate Similarity	NPC474816
0.8286	Intermediate Similarity	NPC315843
0.8281	Intermediate Similarity	NPC26810
0.8281	Intermediate Similarity	NPC55376
0.8226	Intermediate Similarity	NPC249850
0.8226	Intermediate Similarity	NPC129150
0.8226	Intermediate Similarity	NPC135863
0.8226	Intermediate Similarity	NPC293437
0.8194	Intermediate Similarity	NPC262747
0.8154	Intermediate Similarity	NPC473737
0.8116	Intermediate Similarity	NPC476037
0.8095	Intermediate Similarity	NPC254095
0.8088	Intermediate Similarity	NPC474823
0.8088	Intermediate Similarity	NPC238223
0.806	Intermediate Similarity	NPC276299
0.8028	Intermediate Similarity	NPC114727
0.8028	Intermediate Similarity	NPC476590
0.8028	Intermediate Similarity	NPC107654
0.8	Intermediate Similarity	NPC293114
0.8	Intermediate Similarity	NPC151648
0.8	Intermediate Similarity	NPC475944
0.7971	Intermediate Similarity	NPC475004
0.7969	Intermediate Similarity	NPC97570
0.7941	Intermediate Similarity	NPC132286
0.7941	Intermediate Similarity	NPC203335
0.7937	Intermediate Similarity	NPC294938
0.7917	Intermediate Similarity	NPC478191
0.7917	Intermediate Similarity	NPC478192
0.7917	Intermediate Similarity	NPC478193
0.7917	Intermediate Similarity	NPC478195
0.7917	Intermediate Similarity	NPC478194
0.7917	Intermediate Similarity	NPC478196
0.791	Intermediate Similarity	NPC96414
0.791	Intermediate Similarity	NPC19769
0.7895	Intermediate Similarity	NPC323251
0.7887	Intermediate Similarity	NPC284006
0.7887	Intermediate Similarity	NPC329890
0.7857	Intermediate Similarity	NPC329904
0.7857	Intermediate Similarity	NPC476012
0.7857	Intermediate Similarity	NPC473361
0.7857	Intermediate Similarity	NPC4299
0.7812	Intermediate Similarity	NPC21946
0.7794	Intermediate Similarity	NPC201356
0.7794	Intermediate Similarity	NPC248125
0.7792	Intermediate Similarity	NPC474809
0.7778	Intermediate Similarity	NPC470686
0.7746	Intermediate Similarity	NPC477086
0.7746	Intermediate Similarity	NPC477087
0.7733	Intermediate Similarity	NPC99651
0.7714	Intermediate Similarity	NPC151481
0.7714	Intermediate Similarity	NPC101622
0.7703	Intermediate Similarity	NPC51809
0.7703	Intermediate Similarity	NPC125365
0.7703	Intermediate Similarity	NPC176329
0.7703	Intermediate Similarity	NPC49302
0.7703	Intermediate Similarity	NPC474818
0.7692	Intermediate Similarity	NPC82465
0.7692	Intermediate Similarity	NPC31086
0.7692	Intermediate Similarity	NPC474865
0.7692	Intermediate Similarity	NPC126518
0.7692	Intermediate Similarity	NPC286189
0.7681	Intermediate Similarity	NPC122627
0.7681	Intermediate Similarity	NPC478097
0.7647	Intermediate Similarity	NPC478099
0.7647	Intermediate Similarity	NPC273600
0.7647	Intermediate Similarity	NPC478098
0.7639	Intermediate Similarity	NPC329914
0.7639	Intermediate Similarity	NPC222244
0.7639	Intermediate Similarity	NPC477085
0.7639	Intermediate Similarity	NPC16349
0.7639	Intermediate Similarity	NPC144419
0.7639	Intermediate Similarity	NPC327383
0.7639	Intermediate Similarity	NPC185186
0.7612	Intermediate Similarity	NPC475073
0.7606	Intermediate Similarity	NPC202011
0.7606	Intermediate Similarity	NPC59558
0.76	Intermediate Similarity	NPC279214
0.76	Intermediate Similarity	NPC221095
0.76	Intermediate Similarity	NPC473471
0.7595	Intermediate Similarity	NPC163606
0.7576	Intermediate Similarity	NPC79756
0.7571	Intermediate Similarity	NPC63873
0.7568	Intermediate Similarity	NPC188860
0.7568	Intermediate Similarity	NPC205615
0.7568	Intermediate Similarity	NPC203277
0.7568	Intermediate Similarity	NPC301207
0.7568	Intermediate Similarity	NPC16279
0.7568	Intermediate Similarity	NPC256640
0.7568	Intermediate Similarity	NPC469880
0.7568	Intermediate Similarity	NPC477202
0.7568	Intermediate Similarity	NPC68819
0.7564	Intermediate Similarity	NPC229799
0.7564	Intermediate Similarity	NPC284472
0.7564	Intermediate Similarity	NPC286770
0.7564	Intermediate Similarity	NPC42476
0.7538	Intermediate Similarity	NPC474084
0.7536	Intermediate Similarity	NPC478101
0.75	Intermediate Similarity	NPC470808
0.75	Intermediate Similarity	NPC472254
0.7467	Intermediate Similarity	NPC233071
0.7467	Intermediate Similarity	NPC477203
0.7465	Intermediate Similarity	NPC88877
0.7465	Intermediate Similarity	NPC476591
0.7465	Intermediate Similarity	NPC475982
0.7436	Intermediate Similarity	NPC11383
0.7436	Intermediate Similarity	NPC471298
0.7436	Intermediate Similarity	NPC310450
0.7436	Intermediate Similarity	NPC474959
0.7436	Intermediate Similarity	NPC475046
0.7432	Intermediate Similarity	NPC327041
0.7432	Intermediate Similarity	NPC329852
0.7432	Intermediate Similarity	NPC260396
0.7432	Intermediate Similarity	NPC161038
0.7432	Intermediate Similarity	NPC285840
0.7429	Intermediate Similarity	NPC478100
0.7429	Intermediate Similarity	NPC472266
0.7391	Intermediate Similarity	NPC471566
0.7391	Intermediate Similarity	NPC182794
0.7391	Intermediate Similarity	NPC471556
0.7391	Intermediate Similarity	NPC471565
0.7368	Intermediate Similarity	NPC93763
0.7368	Intermediate Similarity	NPC279532
0.7368	Intermediate Similarity	NPC108816
0.7368	Intermediate Similarity	NPC248775
0.7353	Intermediate Similarity	NPC44343
0.7353	Intermediate Similarity	NPC210303
0.7353	Intermediate Similarity	NPC179087
0.7342	Intermediate Similarity	NPC116543
0.7342	Intermediate Similarity	NPC40746
0.7342	Intermediate Similarity	NPC169575
0.7342	Intermediate Similarity	NPC471297
0.7333	Intermediate Similarity	NPC127118
0.7333	Intermediate Similarity	NPC209113
0.7324	Intermediate Similarity	NPC287705
0.7317	Intermediate Similarity	NPC474629
0.7313	Intermediate Similarity	NPC98519
0.7313	Intermediate Similarity	NPC26223
0.7313	Intermediate Similarity	NPC130953
0.7308	Intermediate Similarity	NPC112868
0.7308	Intermediate Similarity	NPC150502
0.7308	Intermediate Similarity	NPC315731
0.7297	Intermediate Similarity	NPC474758
0.7286	Intermediate Similarity	NPC475675
0.7286	Intermediate Similarity	NPC475555
0.7273	Intermediate Similarity	NPC139712
0.7273	Intermediate Similarity	NPC470149
0.7273	Intermediate Similarity	NPC1180
0.7273	Intermediate Similarity	NPC180725
0.7273	Intermediate Similarity	NPC470148
0.726	Intermediate Similarity	NPC84038
0.725	Intermediate Similarity	NPC186155
0.725	Intermediate Similarity	NPC78673
0.725	Intermediate Similarity	NPC163093
0.725	Intermediate Similarity	NPC160517
0.7246	Intermediate Similarity	NPC25747
0.7246	Intermediate Similarity	NPC308457
0.7246	Intermediate Similarity	NPC148233
0.7237	Intermediate Similarity	NPC320630
0.7237	Intermediate Similarity	NPC84360
0.7237	Intermediate Similarity	NPC116177
0.7237	Intermediate Similarity	NPC7563
0.7237	Intermediate Similarity	NPC473756
0.7237	Intermediate Similarity	NPC275530
0.7231	Intermediate Similarity	NPC324224
0.7231	Intermediate Similarity	NPC472808
0.7222	Intermediate Similarity	NPC236208
0.7215	Intermediate Similarity	NPC473712
0.7215	Intermediate Similarity	NPC94875
0.7215	Intermediate Similarity	NPC180363
0.7215	Intermediate Similarity	NPC471296
0.7215	Intermediate Similarity	NPC473529
0.7215	Intermediate Similarity	NPC473780
0.7215	Intermediate Similarity	NPC145914
0.7215	Intermediate Similarity	NPC11332
0.7215	Intermediate Similarity	NPC73310
0.7215	Intermediate Similarity	NPC475159
0.7215	Intermediate Similarity	NPC131002
0.7215	Intermediate Similarity	NPC329829
0.7215	Intermediate Similarity	NPC65930
0.7215	Intermediate Similarity	NPC324170
0.7215	Intermediate Similarity	NPC26624
0.7206	Intermediate Similarity	NPC15193
0.7195	Intermediate Similarity	NPC45409
0.7195	Intermediate Similarity	NPC178215
0.7183	Intermediate Similarity	NPC194871
0.7179	Intermediate Similarity	NPC470147
0.7179	Intermediate Similarity	NPC133226
0.7179	Intermediate Similarity	NPC47653
0.7167	Intermediate Similarity	NPC308331
0.7167	Intermediate Similarity	NPC197467
0.7167	Intermediate Similarity	NPC128280
0.7164	Intermediate Similarity	NPC322186
0.7164	Intermediate Similarity	NPC302564

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 NPC282760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	2873
0.2-0.3	4135
0.3-0.4	1590
0.4-0.5	302
0.5-0.6	93
0.6-0.7	20
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7692	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6927	Phase 3
0.7015	Intermediate Similarity	NPD69	Approved
0.7015	Intermediate Similarity	NPD9119	Approved
0.7	Intermediate Similarity	NPD4265	Approved
0.6901	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD9118	Approved
0.6812	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD585	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD4220	Pre-registration
0.6552	Remote Similarity	NPD7838	Discovery
0.6552	Remote Similarity	NPD6698	Approved
0.6552	Remote Similarity	NPD46	Approved
0.6522	Remote Similarity	NPD6109	Phase 1
0.65	Remote Similarity	NPD4271	Approved
0.65	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD5785	Approved
0.6353	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4820	Approved
0.6341	Remote Similarity	NPD4822	Approved
0.6341	Remote Similarity	NPD4819	Approved
0.6341	Remote Similarity	NPD4821	Approved
0.631	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD5343	Approved
0.6237	Remote Similarity	NPD4225	Approved
0.6207	Remote Similarity	NPD4251	Approved
0.6207	Remote Similarity	NPD4250	Approved
0.6173	Remote Similarity	NPD4756	Discovery
0.6163	Remote Similarity	NPD5363	Approved
0.6145	Remote Similarity	NPD4252	Approved
0.6129	Remote Similarity	NPD9411	Phase 1
0.6118	Remote Similarity	NPD5332	Approved
0.6118	Remote Similarity	NPD5331	Approved
0.6111	Remote Similarity	NPD7637	Suspended
0.6105	Remote Similarity	NPD5344	Discontinued
0.6098	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4249	Approved
0.6071	Remote Similarity	NPD4790	Discontinued
0.6064	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6096	Approved
0.6032	Remote Similarity	NPD6097	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD5209	Approved
0.5938	Remote Similarity	NPD39	Approved
0.5938	Remote Similarity	NPD4222	Approved
0.5934	Remote Similarity	NPD7983	Approved
0.5915	Remote Similarity	NPD8779	Phase 3
0.5914	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5786	Approved
0.5895	Remote Similarity	NPD7638	Approved
0.5873	Remote Similarity	NPD5326	Phase 3
0.587	Remote Similarity	NPD5779	Approved
0.587	Remote Similarity	NPD5778	Approved
0.5867	Remote Similarity	NPD3197	Phase 1
0.5867	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6648	Approved
0.5821	Remote Similarity	NPD2268	Discontinued
0.5814	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6435	Approved
0.5784	Remote Similarity	NPD6371	Approved
0.5747	Remote Similarity	NPD6110	Phase 1
0.5743	Remote Similarity	NPD6686	Approved
0.5714	Remote Similarity	NPD5370	Suspended
0.5698	Remote Similarity	NPD5369	Approved
0.5684	Remote Similarity	NPD7839	Suspended
0.5672	Remote Similarity	NPD3173	Approved
0.5644	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7505	Discontinued
0.56	Remote Similarity	NPD4194	Approved
0.56	Remote Similarity	NPD4192	Approved
0.56	Remote Similarity	NPD4193	Approved
0.56	Remote Similarity	NPD4191	Approved
0.56	Remote Similarity	NPD368	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