NPASS Compound

Structure

NPC475748 OpenBabel07101719512D 35 37 0 0 1 0 0 0 0 0999 V2000 1.0444 -5.8579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7662 -2.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1462 -3.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9181 -5.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1497 -5.7706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2996 0.8217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8609 -0.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -4.7943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4743 -1.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -4.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7941 -0.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2626 -4.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1934 -4.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6989 -2.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6999 -4.8222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2836 -5.2706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2304 1.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 -3.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4176 -3.7706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8632 -0.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7124 -2.8151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5633 -1.8262 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1595 -2.0913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6308 -5.1876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4176 -5.7706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3795 2.1759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1483 -1.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5509 -3.8334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2836 -4.2706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0123 0.5636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4577 -1.3789 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 14 19 1 0 0 0 0 15 25 1 0 0 0 0 16 27 2 0 0 0 0 16 31 1 0 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 31 1 1 0 0 0 20 22 1 0 0 0 0 20 32 1 1 0 0 0 21 26 1 6 0 0 0 21 33 1 0 0 0 0 22 15 1 1 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 1 0 0 0 24 26 1 6 0 0 0 24 35 1 0 0 0 0 25 30 2 0 0 0 0 25 34 1 0 0 0 0 26 7 1 6 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.22
Volume:	493.24
LogP:	2.382
LogD:	1.753
LogS:	-4.073
# Rotatable Bonds:	6
TPSA:	117.73
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	5.299
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.896
MDCK Permeability:	0.00014496255607809871
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.901
20% Bioavailability (F20%):	0.372
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	81.28760528564453%
Volume Distribution (VD):	1.209
Pgp-substrate:	21.34769058227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.424
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.382
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	3.862
Half-life (T1/2):	0.544

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.884
AMES Toxicity:	0.188
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.928
Carcinogencity:	0.064
Eye Corrosion:	0.081
Eye Irritation:	0.02
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC475748

Natural Product ID:	NPC475748
*Common Name:**	Crassolide
IUPAC Name:	n.a.
Synonyms:	Crassolide
Standard InCHIKey:	OBGWQFODBKAPHA-KZIGAWSFSA-N
Standard InCHI:	InChI=1S/C26H34O9/c1-13-8-10-19(31-16(4)27)14(2)9-11-21(33-18(6)29)26(7)24(35-26)23-22(15(3)25(30)34-23)20(12-13)32-17(5)28/h8-9,19-24H,3,10-12H2,1-2,4-7H3/b13-8+,14-9+/t19-,20+,21+,22+,23+,24-,26-/m0/s1
SMILES:	C/C/1=CC[C@@H](/C(=C/C[C@H]([C@@]2(C)[C@H]([C@H]3[C@H](C(=C)C(=O)O3)[C@@H](C1)OC(=O)C)O2)OC(=O)C)/C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513920
PubChem CID:	44584717
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[11141104]
NPO2903	Lobophytum michaelae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1360492]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067165]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125220]
NPO2903	Lobophytum michaelae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17473465]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[22014827]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2903	Lobophytum michaelae	Species	n.a.	n.a.	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
ED50	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.39	ug ml-1	PMID[515255]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.26	ug ml-1	PMID[515255]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.85	ug ml-1	PMID[515255]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.08	ug ml-1	PMID[515255]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.29	ug ml-1	PMID[515256]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	4.97	ug ml-1	PMID[515256]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8.35	ug ml-1	PMID[515256]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.14	ug ml-1	PMID[515256]

☑ 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 NPC475748 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	239
0.1-0.2	1484
0.2-0.3	5358
0.3-0.4	10908
0.4-0.5	13019
0.5-0.6	7169
0.6-0.7	3230
0.7-0.8	1100
0.8-0.85	99
0.85-0.9	60
0.9-0.95	25
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC231889
0.9438	High Similarity	NPC476315
0.9419	High Similarity	NPC151770
0.9318	High Similarity	NPC476300
0.9213	High Similarity	NPC473330
0.9213	High Similarity	NPC473316
0.9195	High Similarity	NPC166919
0.9167	High Similarity	NPC272814
0.9111	High Similarity	NPC36954
0.9111	High Similarity	NPC270013
0.9111	High Similarity	NPC14961
0.9101	High Similarity	NPC212486
0.9091	High Similarity	NPC51004
0.907	High Similarity	NPC50637
0.9	High Similarity	NPC474035
0.9	High Similarity	NPC81386
0.9	High Similarity	NPC471147
0.8989	High Similarity	NPC30515
0.8989	High Similarity	NPC184463
0.8977	High Similarity	NPC307411
0.8966	High Similarity	NPC475703
0.8953	High Similarity	NPC50362
0.8953	High Similarity	NPC38468
0.8953	High Similarity	NPC319795
0.8929	High Similarity	NPC141810
0.8901	High Similarity	NPC475659
0.8889	High Similarity	NPC475912
0.883	High Similarity	NPC264477
0.883	High Similarity	NPC477511
0.8817	High Similarity	NPC279561
0.8804	High Similarity	NPC17585
0.8804	High Similarity	NPC473859
0.8804	High Similarity	NPC279621
0.8791	High Similarity	NPC140543
0.8791	High Similarity	NPC303942
0.8791	High Similarity	NPC57405
0.8778	High Similarity	NPC20713
0.875	High Similarity	NPC5130
0.8723	High Similarity	NPC288876
0.8721	High Similarity	NPC474472
0.8721	High Similarity	NPC257358
0.871	High Similarity	NPC471140
0.869	High Similarity	NPC617
0.8681	High Similarity	NPC81419
0.8681	High Similarity	NPC179746
0.8667	High Similarity	NPC329857
0.8667	High Similarity	NPC474761
0.8667	High Similarity	NPC49342
0.8667	High Similarity	NPC312042
0.8667	High Similarity	NPC62815
0.8667	High Similarity	NPC476004
0.8667	High Similarity	NPC469718
0.8667	High Similarity	NPC251385
0.8652	High Similarity	NPC202672
0.8617	High Similarity	NPC473326
0.8617	High Similarity	NPC208233
0.8602	High Similarity	NPC35498
0.8587	High Similarity	NPC476267
0.8587	High Similarity	NPC474247
0.8571	High Similarity	NPC12172
0.8571	High Similarity	NPC208886
0.8557	High Similarity	NPC477510
0.8557	High Similarity	NPC471143
0.8526	High Similarity	NPC477512
0.8523	High Similarity	NPC474547
0.8523	High Similarity	NPC47958
0.8523	High Similarity	NPC304509
0.8523	High Similarity	NPC149725
0.8506	High Similarity	NPC170286
0.8506	High Similarity	NPC170377
0.8495	Intermediate Similarity	NPC474947
0.8495	Intermediate Similarity	NPC471141
0.8478	Intermediate Similarity	NPC228451
0.8478	Intermediate Similarity	NPC475838
0.8478	Intermediate Similarity	NPC125674
0.8469	Intermediate Similarity	NPC223450
0.8462	Intermediate Similarity	NPC80875
0.8452	Intermediate Similarity	NPC97516
0.8438	Intermediate Similarity	NPC476270
0.8427	Intermediate Similarity	NPC284902
0.8421	Intermediate Similarity	NPC474213
0.8409	Intermediate Similarity	NPC470238
0.8409	Intermediate Similarity	NPC138647
0.8404	Intermediate Similarity	NPC230800
0.8384	Intermediate Similarity	NPC477513
0.8372	Intermediate Similarity	NPC474981
0.8367	Intermediate Similarity	NPC474741
0.8352	Intermediate Similarity	NPC474032
0.8352	Intermediate Similarity	NPC92974
0.8351	Intermediate Similarity	NPC149371
0.8333	Intermediate Similarity	NPC475949
0.8315	Intermediate Similarity	NPC197903
0.8315	Intermediate Similarity	NPC99395
0.8298	Intermediate Similarity	NPC471142
0.8283	Intermediate Similarity	NPC243998
0.8276	Intermediate Similarity	NPC301477
0.8276	Intermediate Similarity	NPC207188
0.8276	Intermediate Similarity	NPC25684
0.8276	Intermediate Similarity	NPC281949
0.8261	Intermediate Similarity	NPC473619
0.8247	Intermediate Similarity	NPC201718
0.8247	Intermediate Similarity	NPC15993
0.8247	Intermediate Similarity	NPC473332
0.8247	Intermediate Similarity	NPC47880
0.8247	Intermediate Similarity	NPC164598
0.8247	Intermediate Similarity	NPC474339
0.8242	Intermediate Similarity	NPC58219
0.8242	Intermediate Similarity	NPC227379
0.8242	Intermediate Similarity	NPC474471
0.8242	Intermediate Similarity	NPC177629
0.8242	Intermediate Similarity	NPC281516
0.8229	Intermediate Similarity	NPC471144
0.8222	Intermediate Similarity	NPC204048
0.8222	Intermediate Similarity	NPC474762
0.8222	Intermediate Similarity	NPC476015
0.8211	Intermediate Similarity	NPC476275
0.82	Intermediate Similarity	NPC474716
0.8172	Intermediate Similarity	NPC70251
0.8172	Intermediate Similarity	NPC475881
0.8172	Intermediate Similarity	NPC470379
0.8172	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC470373
0.8163	Intermediate Similarity	NPC320019
0.8163	Intermediate Similarity	NPC324017
0.8163	Intermediate Similarity	NPC471148
0.8161	Intermediate Similarity	NPC474739
0.8161	Intermediate Similarity	NPC474510
0.8152	Intermediate Similarity	NPC295312
0.8152	Intermediate Similarity	NPC4986
0.8132	Intermediate Similarity	NPC266957
0.8132	Intermediate Similarity	NPC248602
0.8132	Intermediate Similarity	NPC186148
0.8125	Intermediate Similarity	NPC40812
0.8111	Intermediate Similarity	NPC137033
0.8111	Intermediate Similarity	NPC215364
0.8111	Intermediate Similarity	NPC21469
0.8105	Intermediate Similarity	NPC107476
0.8105	Intermediate Similarity	NPC224689
0.81	Intermediate Similarity	NPC470975
0.81	Intermediate Similarity	NPC470979
0.81	Intermediate Similarity	NPC103088
0.8095	Intermediate Similarity	NPC140287
0.809	Intermediate Similarity	NPC250315
0.809	Intermediate Similarity	NPC475947
0.809	Intermediate Similarity	NPC318468
0.809	Intermediate Similarity	NPC11620
0.809	Intermediate Similarity	NPC475842
0.8085	Intermediate Similarity	NPC273579
0.8085	Intermediate Similarity	NPC162205
0.8085	Intermediate Similarity	NPC295204
0.8085	Intermediate Similarity	NPC288240
0.8081	Intermediate Similarity	NPC19239
0.8081	Intermediate Similarity	NPC472755
0.8081	Intermediate Similarity	NPC475945
0.8081	Intermediate Similarity	NPC475871
0.8081	Intermediate Similarity	NPC474166
0.8065	Intermediate Similarity	NPC144133
0.8065	Intermediate Similarity	NPC475855
0.8065	Intermediate Similarity	NPC179394
0.8061	Intermediate Similarity	NPC474742
0.8058	Intermediate Similarity	NPC475495
0.8043	Intermediate Similarity	NPC224652
0.8043	Intermediate Similarity	NPC473715
0.8043	Intermediate Similarity	NPC153805
0.8043	Intermediate Similarity	NPC475902
0.8041	Intermediate Similarity	NPC308567
0.8041	Intermediate Similarity	NPC261377
0.8041	Intermediate Similarity	NPC255592
0.8041	Intermediate Similarity	NPC187268
0.8039	Intermediate Similarity	NPC471934
0.8023	Intermediate Similarity	NPC141789
0.8023	Intermediate Similarity	NPC470240
0.8023	Intermediate Similarity	NPC171204
0.8023	Intermediate Similarity	NPC476028
0.8023	Intermediate Similarity	NPC476794
0.8022	Intermediate Similarity	NPC470242
0.8022	Intermediate Similarity	NPC474949
0.8022	Intermediate Similarity	NPC469483
0.8022	Intermediate Similarity	NPC122502
0.8022	Intermediate Similarity	NPC474045
0.8022	Intermediate Similarity	NPC261253
0.8022	Intermediate Similarity	NPC475019
0.8022	Intermediate Similarity	NPC469676
0.8021	Intermediate Similarity	NPC158416
0.8021	Intermediate Similarity	NPC31645
0.8021	Intermediate Similarity	NPC39859
0.8021	Intermediate Similarity	NPC470883
0.8021	Intermediate Similarity	NPC76862
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC100487
0.8	Intermediate Similarity	NPC190294
0.8	Intermediate Similarity	NPC475963
0.8	Intermediate Similarity	NPC3464
0.8	Intermediate Similarity	NPC151176
0.8	Intermediate Similarity	NPC477131
0.8	Intermediate Similarity	NPC474780
0.8	Intermediate Similarity	NPC71589
0.8	Intermediate Similarity	NPC72464
0.7981	Intermediate Similarity	NPC477093
0.7981	Intermediate Similarity	NPC475277

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 NPC475748 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	2053
0.2-0.3	3828
0.3-0.4	2061
0.4-0.5	673
0.5-0.6	255
0.6-0.7	55
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8953	High Similarity	NPD1733	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD46	Approved
0.8261	Intermediate Similarity	NPD6698	Approved
0.8152	Intermediate Similarity	NPD1695	Approved
0.7872	Intermediate Similarity	NPD7838	Discovery
0.7843	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7983	Approved
0.7453	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6686	Approved
0.7087	Intermediate Similarity	NPD6648	Approved
0.7019	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6008	Approved
0.6847	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8516	Approved
0.681	Remote Similarity	NPD8515	Approved
0.681	Remote Similarity	NPD8517	Approved
0.681	Remote Similarity	NPD8513	Phase 3
0.6804	Remote Similarity	NPD1694	Approved
0.6771	Remote Similarity	NPD7154	Phase 3
0.6695	Remote Similarity	NPD7642	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6635	Remote Similarity	NPD7839	Suspended
0.6634	Remote Similarity	NPD5785	Approved
0.6609	Remote Similarity	NPD7115	Discovery
0.6602	Remote Similarity	NPD5282	Discontinued
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5786	Approved
0.6566	Remote Similarity	NPD4249	Approved
0.6555	Remote Similarity	NPD7830	Approved
0.6555	Remote Similarity	NPD7829	Approved
0.6529	Remote Similarity	NPD8074	Phase 3
0.6495	Remote Similarity	NPD5209	Approved
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4820	Approved
0.6458	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5368	Approved
0.6452	Remote Similarity	NPD8039	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6392	Remote Similarity	NPD5369	Approved
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6355	Remote Similarity	NPD7638	Approved
0.6328	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4270	Approved
0.6327	Remote Similarity	NPD4269	Approved
0.632	Remote Similarity	NPD7260	Phase 2
0.6311	Remote Similarity	NPD8451	Approved
0.6311	Remote Similarity	NPD8273	Phase 1
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6271	Remote Similarity	NPD7641	Discontinued
0.6261	Remote Similarity	NPD8297	Approved
0.626	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD4268	Approved
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6399	Phase 3
0.6174	Remote Similarity	NPD6650	Approved
0.6174	Remote Similarity	NPD6649	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6142	Remote Similarity	NPD6845	Suspended
0.614	Remote Similarity	NPD6373	Approved
0.614	Remote Similarity	NPD6372	Approved
0.6122	Remote Similarity	NPD4252	Approved
0.6116	Remote Similarity	NPD8444	Approved
0.6111	Remote Similarity	NPD8392	Approved
0.6111	Remote Similarity	NPD8390	Approved
0.6111	Remote Similarity	NPD8391	Approved
0.6098	Remote Similarity	NPD8342	Approved
0.6098	Remote Similarity	NPD8340	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6098	Remote Similarity	NPD8341	Approved
0.6098	Remote Similarity	NPD8299	Approved
0.6082	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7521	Approved
0.6078	Remote Similarity	NPD6684	Approved
0.6078	Remote Similarity	NPD6409	Approved
0.6078	Remote Similarity	NPD5330	Approved
0.6078	Remote Similarity	NPD7146	Approved
0.6078	Remote Similarity	NPD7334	Approved
0.6078	Remote Similarity	NPD6422	Discontinued
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4632	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.6033	Remote Similarity	NPD6054	Approved
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD7078	Approved
0.5983	Remote Similarity	NPD6882	Approved
0.5981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7900	Approved
0.5965	Remote Similarity	NPD5697	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5962	Remote Similarity	NPD5737	Approved
0.5962	Remote Similarity	NPD6903	Approved
0.5962	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6672	Approved
0.5952	Remote Similarity	NPD7736	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5948	Remote Similarity	NPD2067	Discontinued
0.5943	Remote Similarity	NPD5693	Phase 1
0.5943	Remote Similarity	NPD7637	Suspended
0.5941	Remote Similarity	NPD5331	Approved
0.5941	Remote Similarity	NPD5332	Approved
0.5941	Remote Similarity	NPD6110	Phase 1
0.5935	Remote Similarity	NPD6370	Approved
0.5934	Remote Similarity	NPD7331	Phase 2
0.5932	Remote Similarity	NPD8133	Approved
0.5917	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6009	Approved
0.5917	Remote Similarity	NPD7500	Approved
0.5913	Remote Similarity	NPD7320	Approved
0.5905	Remote Similarity	NPD6051	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.59	Remote Similarity	NPD4790	Discontinued
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD2204	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD8328	Phase 3
0.5882	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD8293	Discontinued
0.587	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7327	Approved
0.5868	Remote Similarity	NPD7328	Approved
0.5865	Remote Similarity	NPD3573	Approved
0.5862	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD6012	Approved
0.5862	Remote Similarity	NPD6013	Approved
0.5854	Remote Similarity	NPD6015	Approved
0.5854	Remote Similarity	NPD8266	Approved
0.5854	Remote Similarity	NPD6016	Approved
0.5854	Remote Similarity	NPD8268	Approved
0.5854	Remote Similarity	NPD8269	Approved
0.5854	Remote Similarity	NPD8033	Approved
0.5854	Remote Similarity	NPD8267	Approved
0.5854	Remote Similarity	NPD5983	Phase 2
0.5854	Remote Similarity	NPD7503	Approved
0.5849	Remote Similarity	NPD3168	Discontinued
0.5842	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD5701	Approved
0.5824	Remote Similarity	NPD7341	Phase 2
0.582	Remote Similarity	NPD7516	Approved
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5818	Remote Similarity	NPD7902	Approved
0.5812	Remote Similarity	NPD6421	Discontinued
0.5806	Remote Similarity	NPD5988	Approved
0.5806	Remote Similarity	NPD8080	Discontinued
0.5794	Remote Similarity	NPD6336	Discontinued
0.5785	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5695	Phase 3
0.5776	Remote Similarity	NPD6011	Approved
0.5772	Remote Similarity	NPD8294	Approved
0.5772	Remote Similarity	NPD8377	Approved
0.5766	Remote Similarity	NPD5696	Approved
0.5755	Remote Similarity	NPD6904	Approved
0.5755	Remote Similarity	NPD6080	Approved
0.5755	Remote Similarity	NPD5370	Suspended
0.5755	Remote Similarity	NPD6673	Approved
0.5752	Remote Similarity	NPD7632	Discontinued
0.5728	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8378	Approved
0.5726	Remote Similarity	NPD8379	Approved
0.5726	Remote Similarity	NPD8335	Approved
0.5726	Remote Similarity	NPD6921	Approved
0.5726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8380	Approved
0.5726	Remote Similarity	NPD8296	Approved
0.5714	Remote Similarity	NPD7524	Approved
0.5703	Remote Similarity	NPD8336	Approved
0.5703	Remote Similarity	NPD8337	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