NPASS Compound

Structure

CID181587 OpenBabel06191715552D 23 24 0 0 1 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8228 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3733 -0.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6742 -1.1173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0123 -0.0858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2711 -1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0464 0.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5640 -1.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3393 -0.5341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 15 20 1 0 0 0 0 16 20 1 6 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	4.887
LogD:	4.099
LogS:	-5.114
# Rotatable Bonds:	5
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	3.903
Fsp3:	0.55
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:	-4.68
MDCK Permeability:	2.0763351130881347e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.491

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.69669342041016%
Volume Distribution (VD):	3.254
Pgp-substrate:	4.931641578674316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.696
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.76
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.345
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	10.812
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.414
Skin Sensitization:	0.751
Carcinogencity:	0.248
Eye Corrosion:	0.726
Eye Irritation:	0.84
Respiratory Toxicity:	0.471

Download Data

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

Natural Product: NPC181587

Natural Product ID:	NPC181587
*Common Name:**	Sollasin D
IUPAC Name:	4-methoxy-6-[(E)-2-methyl-4-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]but-1-enyl]pyran-2-one
Synonyms:	Sollasin D
Standard InCHIKey:	NCBOYBRBUGFNGR-RRHMOEORSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14(11-18-12-17(22-5)13-19(21)23-18)9-10-20(4)15(2)7-6-8-16(20)3/h7,11-13,16H,6,8-10H2,1-5H3/b14-11+/t16-,20-/m1/s1
SMILES:	C/C(=Cc1cc(cc(=O)o1)OC)/CC[C@]1(C)C(=CCC[C@H]1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483420
PubChem CID:	10335934
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives

*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
NPO8264	Holothuria scabra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18087805]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[28294414]
NPO4135	Poecillastra sollasi	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496702]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7239	Gnetum parvifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7239	Gnetum parvifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4135	Poecillastra sollasi	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3550	Clerodendrum phlomidis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7239	Gnetum parvifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5112	Adonis leiosepala	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21035	Crinum oliganthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO606	Felicia filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2032	Eucalyptus aggregata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2227	Clerodendrum splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8264	Holothuria scabra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8799	Quassia multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1304	Macrozamia macdonnelli	Species	Zamiaceae	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	5.5	ug.mL-1	PMID[492291]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11.3	ug.mL-1	PMID[492291]
NPT2	Others	Unspecified		IC50	=	42000.0	nM	PMID[492291]

☑ 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 NPC181587 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	325
0.1-0.2	1638
0.2-0.3	4808
0.3-0.4	11005
0.4-0.5	8360
0.5-0.6	6749
0.6-0.7	7759
0.7-0.8	1920
0.8-0.85	92
0.85-0.9	39
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8406	Intermediate Similarity	NPC185587
0.8267	Intermediate Similarity	NPC54996
0.8148	Intermediate Similarity	NPC125925
0.8133	Intermediate Similarity	NPC4509
0.8116	Intermediate Similarity	NPC329698
0.8116	Intermediate Similarity	NPC226066
0.8	Intermediate Similarity	NPC65650
0.7975	Intermediate Similarity	NPC268122
0.7975	Intermediate Similarity	NPC16321
0.7973	Intermediate Similarity	NPC276336
0.7875	Intermediate Similarity	NPC118423
0.7867	Intermediate Similarity	NPC20025
0.7831	Intermediate Similarity	NPC472302
0.7808	Intermediate Similarity	NPC232812
0.7792	Intermediate Similarity	NPC473825
0.775	Intermediate Similarity	NPC94200
0.7722	Intermediate Similarity	NPC268827
0.7711	Intermediate Similarity	NPC163016
0.7711	Intermediate Similarity	NPC75315
0.7703	Intermediate Similarity	NPC37929
0.7703	Intermediate Similarity	NPC316029
0.7703	Intermediate Similarity	NPC64234
0.7692	Intermediate Similarity	NPC105197
0.7639	Intermediate Similarity	NPC242945
0.7639	Intermediate Similarity	NPC191233
0.7639	Intermediate Similarity	NPC259156
0.7595	Intermediate Similarity	NPC190211
0.759	Intermediate Similarity	NPC168248
0.7571	Intermediate Similarity	NPC329416
0.7571	Intermediate Similarity	NPC317177
0.7571	Intermediate Similarity	NPC317025
0.7571	Intermediate Similarity	NPC326645
0.7561	Intermediate Similarity	NPC470800
0.7531	Intermediate Similarity	NPC471218
0.75	Intermediate Similarity	NPC222244
0.75	Intermediate Similarity	NPC16349
0.75	Intermediate Similarity	NPC220766
0.75	Intermediate Similarity	NPC107258
0.7442	Intermediate Similarity	NPC469595
0.7442	Intermediate Similarity	NPC212679
0.7442	Intermediate Similarity	NPC220454
0.7439	Intermediate Similarity	NPC288281
0.7439	Intermediate Similarity	NPC474976
0.7439	Intermediate Similarity	NPC474790
0.7432	Intermediate Similarity	NPC313444
0.7412	Intermediate Similarity	NPC471956
0.7412	Intermediate Similarity	NPC196407
0.7397	Intermediate Similarity	NPC255781
0.7375	Intermediate Similarity	NPC242767
0.7368	Intermediate Similarity	NPC257618
0.7353	Intermediate Similarity	NPC96663
0.7342	Intermediate Similarity	NPC315394
0.7333	Intermediate Similarity	NPC470693
0.7326	Intermediate Similarity	NPC284561
0.7326	Intermediate Similarity	NPC474844
0.7284	Intermediate Similarity	NPC233332
0.7273	Intermediate Similarity	NPC130016
0.7273	Intermediate Similarity	NPC476489
0.7273	Intermediate Similarity	NPC180015
0.7273	Intermediate Similarity	NPC109576
0.7273	Intermediate Similarity	NPC476490
0.7273	Intermediate Similarity	NPC56747
0.7262	Intermediate Similarity	NPC329630
0.7262	Intermediate Similarity	NPC189311
0.7262	Intermediate Similarity	NPC472442
0.725	Intermediate Similarity	NPC471220
0.7241	Intermediate Similarity	NPC469372
0.7241	Intermediate Similarity	NPC221111
0.7241	Intermediate Similarity	NPC280149
0.7237	Intermediate Similarity	NPC315285
0.7229	Intermediate Similarity	NPC474193
0.7229	Intermediate Similarity	NPC472440
0.7229	Intermediate Similarity	NPC42476
0.7229	Intermediate Similarity	NPC311070
0.7229	Intermediate Similarity	NPC193198
0.7229	Intermediate Similarity	NPC477124
0.7229	Intermediate Similarity	NPC12283
0.7215	Intermediate Similarity	NPC27205
0.7195	Intermediate Similarity	NPC25554
0.7191	Intermediate Similarity	NPC120351
0.7191	Intermediate Similarity	NPC471994
0.7191	Intermediate Similarity	NPC166143
0.7176	Intermediate Similarity	NPC220478
0.7176	Intermediate Similarity	NPC471219
0.7162	Intermediate Similarity	NPC315115
0.7143	Intermediate Similarity	NPC318515
0.7143	Intermediate Similarity	NPC133253
0.7143	Intermediate Similarity	NPC96055
0.7143	Intermediate Similarity	NPC474359
0.7126	Intermediate Similarity	NPC210216
0.7125	Intermediate Similarity	NPC316324
0.7125	Intermediate Similarity	NPC189206
0.7125	Intermediate Similarity	NPC262747
0.7111	Intermediate Similarity	NPC295347
0.7108	Intermediate Similarity	NPC256112
0.7108	Intermediate Similarity	NPC200513
0.7093	Intermediate Similarity	NPC477228
0.7089	Intermediate Similarity	NPC228978
0.7089	Intermediate Similarity	NPC476346
0.7079	Intermediate Similarity	NPC242069
0.7079	Intermediate Similarity	NPC469939
0.7073	Intermediate Similarity	NPC469802
0.7073	Intermediate Similarity	NPC160582
0.7067	Intermediate Similarity	NPC472266
0.7067	Intermediate Similarity	NPC254886
0.7065	Intermediate Similarity	NPC181147
0.7059	Intermediate Similarity	NPC42586
0.7059	Intermediate Similarity	NPC474013
0.7059	Intermediate Similarity	NPC473251
0.7045	Intermediate Similarity	NPC280592
0.7045	Intermediate Similarity	NPC213636
0.7045	Intermediate Similarity	NPC212369
0.7045	Intermediate Similarity	NPC310479
0.7045	Intermediate Similarity	NPC253177
0.7045	Intermediate Similarity	NPC273199
0.7045	Intermediate Similarity	NPC182136
0.7037	Intermediate Similarity	NPC474816
0.7037	Intermediate Similarity	NPC184737
0.7037	Intermediate Similarity	NPC209135
0.7033	Intermediate Similarity	NPC16967
0.7033	Intermediate Similarity	NPC260796
0.7033	Intermediate Similarity	NPC112654
0.7027	Intermediate Similarity	NPC471556
0.7024	Intermediate Similarity	NPC469
0.7024	Intermediate Similarity	NPC22611
0.7024	Intermediate Similarity	NPC472377
0.7013	Intermediate Similarity	NPC315597
0.7013	Intermediate Similarity	NPC59558
0.7013	Intermediate Similarity	NPC469660
0.7011	Intermediate Similarity	NPC24816
0.7011	Intermediate Similarity	NPC106332
0.7011	Intermediate Similarity	NPC226863
0.7	Intermediate Similarity	NPC19907
0.7	Intermediate Similarity	NPC40353
0.7	Intermediate Similarity	NPC38830
0.7	Intermediate Similarity	NPC474463
0.7	Intermediate Similarity	NPC473223
0.7	Intermediate Similarity	NPC477130
0.7	Intermediate Similarity	NPC477129
0.7	Intermediate Similarity	NPC191521
0.6988	Remote Similarity	NPC170303
0.6988	Remote Similarity	NPC475833
0.6988	Remote Similarity	NPC40228
0.6986	Remote Similarity	NPC155849
0.6977	Remote Similarity	NPC131813
0.6966	Remote Similarity	NPC471329
0.6966	Remote Similarity	NPC296114
0.6966	Remote Similarity	NPC2882
0.6962	Remote Similarity	NPC470686
0.6962	Remote Similarity	NPC306928
0.6957	Remote Similarity	NPC202705
0.6957	Remote Similarity	NPC208094
0.6951	Remote Similarity	NPC471299
0.6944	Remote Similarity	NPC429928
0.6944	Remote Similarity	NPC19241
0.6941	Remote Similarity	NPC149869
0.6941	Remote Similarity	NPC126518
0.6941	Remote Similarity	NPC475100
0.6933	Remote Similarity	NPC116013
0.6932	Remote Similarity	NPC5509
0.6932	Remote Similarity	NPC173042
0.6932	Remote Similarity	NPC177141
0.6932	Remote Similarity	NPC471654
0.6932	Remote Similarity	NPC470734
0.6923	Remote Similarity	NPC21944
0.6923	Remote Similarity	NPC474909
0.6915	Remote Similarity	NPC194028
0.6915	Remote Similarity	NPC168319
0.6914	Remote Similarity	NPC472300
0.6914	Remote Similarity	NPC473756
0.6914	Remote Similarity	NPC316500
0.6905	Remote Similarity	NPC186276
0.6905	Remote Similarity	NPC324170
0.6901	Remote Similarity	NPC60772
0.6897	Remote Similarity	NPC312561
0.6897	Remote Similarity	NPC476600
0.6897	Remote Similarity	NPC181327
0.6889	Remote Similarity	NPC152778
0.6889	Remote Similarity	NPC1108
0.6889	Remote Similarity	NPC205034
0.6889	Remote Similarity	NPC162615
0.6889	Remote Similarity	NPC472954
0.6883	Remote Similarity	NPC151481
0.6882	Remote Similarity	NPC278673
0.6875	Remote Similarity	NPC68624
0.6867	Remote Similarity	NPC195424
0.686	Remote Similarity	NPC30984
0.686	Remote Similarity	NPC471795
0.686	Remote Similarity	NPC109528
0.686	Remote Similarity	NPC163606
0.686	Remote Similarity	NPC106416
0.686	Remote Similarity	NPC35933
0.686	Remote Similarity	NPC217394
0.686	Remote Similarity	NPC65661
0.686	Remote Similarity	NPC86316
0.6857	Remote Similarity	NPC221763
0.6849	Remote Similarity	NPC469728
0.6835	Remote Similarity	NPC144947
0.6829	Remote Similarity	NPC474005
0.6829	Remote Similarity	NPC4827

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 NPC181587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	985
0.2-0.3	1768
0.3-0.4	2889
0.4-0.5	1879
0.5-0.6	999
0.6-0.7	262
0.7-0.8	54
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4193	Approved
0.7571	Intermediate Similarity	NPD4194	Approved
0.7571	Intermediate Similarity	NPD4192	Approved
0.7571	Intermediate Similarity	NPD4191	Approved
0.7108	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD8039	Approved
0.7027	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5276	Approved
0.6706	Remote Similarity	NPD5209	Approved
0.6556	Remote Similarity	NPD6051	Approved
0.6543	Remote Similarity	NPD5733	Approved
0.6543	Remote Similarity	NPD4687	Approved
0.6543	Remote Similarity	NPD4058	Approved
0.6477	Remote Similarity	NPD1694	Approved
0.6456	Remote Similarity	NPD4137	Phase 3
0.6413	Remote Similarity	NPD5693	Phase 1
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.6389	Remote Similarity	NPD4219	Approved
0.6375	Remote Similarity	NPD4691	Approved
0.6375	Remote Similarity	NPD4747	Approved
0.6304	Remote Similarity	NPD5692	Phase 3
0.6304	Remote Similarity	NPD5207	Approved
0.6265	Remote Similarity	NPD8264	Approved
0.6264	Remote Similarity	NPD6672	Approved
0.6264	Remote Similarity	NPD6903	Approved
0.6264	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5737	Approved
0.6237	Remote Similarity	NPD6050	Approved
0.6237	Remote Similarity	NPD5694	Approved
0.6216	Remote Similarity	NPD287	Approved
0.6186	Remote Similarity	NPD4225	Approved
0.6186	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD3573	Approved
0.6122	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD7639	Approved
0.6087	Remote Similarity	NPD5208	Approved
0.6064	Remote Similarity	NPD7637	Suspended
0.6022	Remote Similarity	NPD6904	Approved
0.6022	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6673	Approved
0.6022	Remote Similarity	NPD6080	Approved
0.5978	Remote Similarity	NPD1282	Approved
0.5946	Remote Similarity	NPD7503	Approved
0.5938	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7748	Approved
0.5938	Remote Similarity	NPD7900	Approved
0.593	Remote Similarity	NPD4756	Discovery
0.5926	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD6927	Phase 3
0.5909	Remote Similarity	NPD4695	Discontinued
0.5895	Remote Similarity	NPD6411	Approved
0.5895	Remote Similarity	NPD5284	Approved
0.5895	Remote Similarity	NPD5281	Approved
0.5889	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5909	Discontinued
0.5876	Remote Similarity	NPD5695	Phase 3
0.5876	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD5654	Approved
0.587	Remote Similarity	NPD6098	Approved
0.587	Remote Similarity	NPD5279	Phase 3
0.5857	Remote Similarity	NPD4220	Pre-registration
0.5857	Remote Similarity	NPD8262	Approved
0.5833	Remote Similarity	NPD5779	Approved
0.5833	Remote Similarity	NPD5778	Approved
0.58	Remote Similarity	NPD6648	Approved
0.5795	Remote Similarity	NPD4195	Approved
0.5794	Remote Similarity	NPD6053	Discontinued
0.5789	Remote Similarity	NPD7838	Discovery
0.5773	Remote Similarity	NPD6001	Approved
0.5761	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD7902	Approved
0.5758	Remote Similarity	NPD5959	Approved
0.5758	Remote Similarity	NPD6083	Phase 2
0.573	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7515	Phase 2
0.5714	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6049	Phase 2
0.5714	Remote Similarity	NPD6686	Approved
0.57	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5696	Approved
0.5699	Remote Similarity	NPD4694	Approved
0.5699	Remote Similarity	NPD5280	Approved
0.5699	Remote Similarity	NPD4623	Approved
0.5699	Remote Similarity	NPD4519	Discontinued
0.5684	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6101	Approved
0.5682	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.567	Remote Similarity	NPD6399	Phase 3
0.5663	Remote Similarity	NPD6923	Approved
0.5663	Remote Similarity	NPD6922	Approved
0.5652	Remote Similarity	NPD3133	Approved
0.5652	Remote Similarity	NPD3665	Phase 1
0.5652	Remote Similarity	NPD3666	Approved
0.5644	Remote Similarity	NPD6404	Discontinued
0.5625	Remote Similarity	NPD5785	Approved
0.5625	Remote Similarity	NPD6698	Approved
0.5625	Remote Similarity	NPD46	Approved
0.5604	Remote Similarity	NPD4223	Phase 3
0.5604	Remote Similarity	NPD4221	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