NPASS Compound

Structure

NPC469576 OpenBabel07101718272D 39 44 0 0 1 0 0 0 0 0999 V2000 -2.8442 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 -0.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2233 -2.3705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0789 3.8382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1855 -0.9729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1424 -1.1763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3289 0.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9769 0.3979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9304 -1.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1896 1.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0467 -0.2991 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8600 2.1580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9304 0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3888 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5054 -0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4919 2.3665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8301 2.0317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3979 -1.8720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3979 0.8937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4844 3.0613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6315 -0.3291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2327 1.2327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 27 1 0 0 0 0 5 36 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 25 1 0 0 0 0 9 37 1 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 37 1 0 0 0 0 13 26 1 0 0 0 0 13 28 1 0 0 0 0 14 30 2 0 0 0 0 14 38 1 0 0 0 0 15 23 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 6 0 0 0 18 27 1 0 0 0 0 19 31 2 0 0 0 0 19 36 1 0 0 0 0 20 32 2 0 0 0 0 20 39 1 0 0 0 0 21 22 1 0 0 0 0 22 29 1 0 0 0 0 22 33 2 0 0 0 0 23 25 1 1 0 0 0 23 39 1 0 0 0 0 24 26 1 6 0 0 0 24 29 1 0 0 0 0 24 38 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 28 1 1 0 0 0 28 29 1 1 0 0 0 28 34 1 0 0 0 0 29 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.2
Volume:	525.612
LogP:	1.81
LogD:	0.853
LogS:	-4.551
# Rotatable Bonds:	6
TPSA:	149.57
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	6.118
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.374
MDCK Permeability:	1.7085507352021523e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.247
Human Intestinal Absorption (HIA):	0.813
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.73
Plasma Protein Binding (PPB):	85.77635192871094%
Volume Distribution (VD):	1.7
Pgp-substrate:	13.290863990783691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.725
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.535

ADMET: Excretion

Clearance (CL):	1.8
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.318
AMES Toxicity:	0.55
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.848
Skin Sensitization:	0.183
Carcinogencity:	0.939
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC469576

Natural Product ID:	NPC469576
*Common Name:**	Moluccensin H
IUPAC Name:	n.a.
Synonyms:	Moluccensin H
Standard InCHIKey:	IGHHWHRZZGJKOP-CCDRIMESSA-N
Standard InCHI:	InChI=1S/C29H32O10/c1-14(30)38-24-26(3)13-28(34)27(4,18(26)11-19(31)36-5)16-6-8-25(2)17(21(16)22(33)29(24,28)35)10-20(32)39-23(25)15-7-9-37-12-15/h7,9-10,12,18,23-24,34-35H,6,8,11,13H2,1-5H3/t18-,23-,24-,25+,26-,27+,28+,29+/m0/s1
SMILES:	COC(=O)C[C@H]1[C@]2(C)C[C@]3([C@]1(C)C1=C(C(=O)[C@]3([C@H]2OC(=O)C)O)C2=CC(=O)O[C@H]([C@@]2(CC1)C)c1ccoc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088035
PubChem CID:	46184327
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT845	Cell Line	BT-474	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[546018]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[546018]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[546018]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[546018]
NPT2	Others	Unspecified		IC50	>	27000.0	nM	PMID[546019]

☑ 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 NPC469576 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	383
0.1-0.2	1550
0.2-0.3	3458
0.3-0.4	6613
0.4-0.5	11334
0.5-0.6	9121
0.6-0.7	8947
0.7-0.8	1111
0.8-0.85	139
0.85-0.9	33
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC469633
0.9632	High Similarity	NPC94763
0.9632	High Similarity	NPC236004
0.9398	High Similarity	NPC478177
0.9277	High Similarity	NPC471437
0.9268	High Similarity	NPC327922
0.9259	High Similarity	NPC165218
0.9207	High Similarity	NPC478179
0.9146	High Similarity	NPC478178
0.9059	High Similarity	NPC470938
0.8929	High Similarity	NPC285227
0.8929	High Similarity	NPC159232
0.8922	High Similarity	NPC472765
0.8922	High Similarity	NPC472766
0.8896	High Similarity	NPC472778
0.8896	High Similarity	NPC472776
0.8896	High Similarity	NPC472777
0.8869	High Similarity	NPC472659
0.8862	High Similarity	NPC472764
0.8802	High Similarity	NPC149945
0.8795	High Similarity	NPC469338
0.8795	High Similarity	NPC292389
0.8793	High Similarity	NPC247563
0.8793	High Similarity	NPC242068
0.878	High Similarity	NPC261597
0.878	High Similarity	NPC36655
0.8773	High Similarity	NPC44675
0.8773	High Similarity	NPC214541
0.875	High Similarity	NPC173516
0.875	High Similarity	NPC476224
0.8743	High Similarity	NPC470940
0.8743	High Similarity	NPC469849
0.8743	High Similarity	NPC276551
0.8735	High Similarity	NPC329938
0.8735	High Similarity	NPC82851
0.8727	High Similarity	NPC475967
0.872	High Similarity	NPC469485
0.8713	High Similarity	NPC471632
0.8698	High Similarity	NPC471397
0.869	High Similarity	NPC470875
0.869	High Similarity	NPC214600
0.869	High Similarity	NPC472141
0.8686	High Similarity	NPC105395
0.8683	High Similarity	NPC224394
0.8683	High Similarity	NPC663
0.8675	High Similarity	NPC477402
0.8667	High Similarity	NPC470118
0.8667	High Similarity	NPC187149
0.8667	High Similarity	NPC173544
0.8659	High Similarity	NPC264943
0.8655	High Similarity	NPC469848
0.8647	High Similarity	NPC470995
0.8639	High Similarity	NPC472774
0.8639	High Similarity	NPC472775
0.8623	High Similarity	NPC472767
0.8623	High Similarity	NPC188649
0.8623	High Similarity	NPC6326
0.8623	High Similarity	NPC472668
0.8623	High Similarity	NPC69028
0.8623	High Similarity	NPC149896
0.8614	High Similarity	NPC477403
0.8614	High Similarity	NPC475226
0.8614	High Similarity	NPC474932
0.8613	High Similarity	NPC470181
0.8588	High Similarity	NPC160651
0.8588	High Similarity	NPC271235
0.8571	High Similarity	NPC472773
0.8571	High Similarity	NPC88841
0.8571	High Similarity	NPC471168
0.8571	High Similarity	NPC472669
0.8571	High Similarity	NPC288602
0.8571	High Similarity	NPC477405
0.8563	High Similarity	NPC470789
0.8563	High Similarity	NPC472653
0.8554	High Similarity	NPC249021
0.8554	High Similarity	NPC197137
0.8554	High Similarity	NPC299038
0.8554	High Similarity	NPC45101
0.8554	High Similarity	NPC195131
0.8545	High Similarity	NPC155939
0.8545	High Similarity	NPC296807
0.8545	High Similarity	NPC141538
0.8537	High Similarity	NPC44577
0.8529	High Similarity	NPC472651
0.8521	High Similarity	NPC271657
0.8521	High Similarity	NPC470182
0.8512	High Similarity	NPC5079
0.8512	High Similarity	NPC470792
0.8512	High Similarity	NPC472771
0.8512	High Similarity	NPC5741
0.8512	High Similarity	NPC200782
0.8512	High Similarity	NPC471166
0.8512	High Similarity	NPC471167
0.8512	High Similarity	NPC197596
0.8512	High Similarity	NPC18347
0.8503	High Similarity	NPC307383
0.8503	High Similarity	NPC472779
0.8497	Intermediate Similarity	NPC477824
0.8494	Intermediate Similarity	NPC204663
0.8488	Intermediate Similarity	NPC169299
0.8488	Intermediate Similarity	NPC160818
0.848	Intermediate Similarity	NPC472652
0.8462	Intermediate Similarity	NPC134254
0.8462	Intermediate Similarity	NPC39986
0.8462	Intermediate Similarity	NPC234660
0.8462	Intermediate Similarity	NPC51568
0.8462	Intermediate Similarity	NPC472139
0.8462	Intermediate Similarity	NPC302369
0.8452	Intermediate Similarity	NPC25255
0.8443	Intermediate Similarity	NPC286722
0.8443	Intermediate Similarity	NPC88007
0.8434	Intermediate Similarity	NPC92979
0.843	Intermediate Similarity	NPC82602
0.843	Intermediate Similarity	NPC472650
0.8424	Intermediate Similarity	NPC33938
0.8424	Intermediate Similarity	NPC469503
0.8424	Intermediate Similarity	NPC246164
0.8424	Intermediate Similarity	NPC476201
0.8421	Intermediate Similarity	NPC476850
0.8421	Intermediate Similarity	NPC472282
0.8421	Intermediate Similarity	NPC476861
0.8415	Intermediate Similarity	NPC470997
0.8412	Intermediate Similarity	NPC123088
0.8412	Intermediate Similarity	NPC476858
0.8412	Intermediate Similarity	NPC476856
0.8412	Intermediate Similarity	NPC259943
0.8412	Intermediate Similarity	NPC476857
0.8402	Intermediate Similarity	NPC193798
0.8402	Intermediate Similarity	NPC68848
0.8402	Intermediate Similarity	NPC263432
0.8393	Intermediate Similarity	NPC475295
0.8393	Intermediate Similarity	NPC473473
0.8393	Intermediate Similarity	NPC472671
0.8383	Intermediate Similarity	NPC209364
0.8382	Intermediate Similarity	NPC475237
0.8382	Intermediate Similarity	NPC475641
0.8373	Intermediate Similarity	NPC98206
0.8373	Intermediate Similarity	NPC34421
0.8373	Intermediate Similarity	NPC253201
0.8373	Intermediate Similarity	NPC30222
0.8373	Intermediate Similarity	NPC237259
0.8373	Intermediate Similarity	NPC282445
0.8373	Intermediate Similarity	NPC302054
0.8372	Intermediate Similarity	NPC296558
0.8372	Intermediate Similarity	NPC472673
0.8364	Intermediate Similarity	NPC18135
0.8364	Intermediate Similarity	NPC116717
0.8363	Intermediate Similarity	NPC121995
0.8354	Intermediate Similarity	NPC69647
0.8354	Intermediate Similarity	NPC472654
0.8354	Intermediate Similarity	NPC234494
0.8354	Intermediate Similarity	NPC471001
0.8354	Intermediate Similarity	NPC125182
0.8353	Intermediate Similarity	NPC285567
0.8353	Intermediate Similarity	NPC469846
0.8344	Intermediate Similarity	NPC255414
0.8343	Intermediate Similarity	NPC335761
0.8343	Intermediate Similarity	NPC191828
0.8333	Intermediate Similarity	NPC194499
0.8333	Intermediate Similarity	NPC472772
0.8333	Intermediate Similarity	NPC214495
0.8333	Intermediate Similarity	NPC475066
0.8333	Intermediate Similarity	NPC470119
0.8333	Intermediate Similarity	NPC167142
0.8333	Intermediate Similarity	NPC195954
0.8333	Intermediate Similarity	NPC472283
0.8323	Intermediate Similarity	NPC35000
0.8323	Intermediate Similarity	NPC469336
0.8323	Intermediate Similarity	NPC471175
0.8323	Intermediate Similarity	NPC476262
0.8314	Intermediate Similarity	NPC476853
0.8313	Intermediate Similarity	NPC472672
0.8313	Intermediate Similarity	NPC268905
0.8313	Intermediate Similarity	NPC470996
0.8304	Intermediate Similarity	NPC261184
0.8304	Intermediate Similarity	NPC476860
0.8303	Intermediate Similarity	NPC156189
0.8303	Intermediate Similarity	NPC196846
0.8294	Intermediate Similarity	NPC18986
0.8294	Intermediate Similarity	NPC211777
0.8294	Intermediate Similarity	NPC117986
0.8294	Intermediate Similarity	NPC96443
0.8294	Intermediate Similarity	NPC290400
0.8294	Intermediate Similarity	NPC470939
0.8274	Intermediate Similarity	NPC175964
0.8274	Intermediate Similarity	NPC471169
0.8274	Intermediate Similarity	NPC107646
0.8274	Intermediate Similarity	NPC126723
0.8263	Intermediate Similarity	NPC178932
0.8263	Intermediate Similarity	NPC57998
0.8256	Intermediate Similarity	NPC93172
0.8256	Intermediate Similarity	NPC97574
0.8256	Intermediate Similarity	NPC23387
0.8256	Intermediate Similarity	NPC475779
0.8253	Intermediate Similarity	NPC272590
0.8246	Intermediate Similarity	NPC283209
0.8246	Intermediate Similarity	NPC198047
0.8242	Intermediate Similarity	NPC470998
0.8242	Intermediate Similarity	NPC195325
0.8239	Intermediate Similarity	NPC262386

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 NPC469576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	1122
0.2-0.3	2411
0.3-0.4	2688
0.4-0.5	1680
0.5-0.6	691
0.6-0.7	209
0.7-0.8	11
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8545	High Similarity	NPD5761	Phase 2
0.8545	High Similarity	NPD5760	Phase 2
0.8212	Intermediate Similarity	NPD8434	Phase 2
0.8129	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6764	Approved
0.7933	Intermediate Similarity	NPD6765	Approved
0.776	Intermediate Similarity	NPD6785	Approved
0.776	Intermediate Similarity	NPD6784	Approved
0.7322	Intermediate Similarity	NPD7799	Discontinued
0.7288	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7075	Discontinued
0.7216	Intermediate Similarity	NPD6599	Discontinued
0.7171	Intermediate Similarity	NPD8404	Phase 2
0.7151	Intermediate Similarity	NPD3817	Phase 2
0.7135	Intermediate Similarity	NPD6801	Discontinued
0.7127	Intermediate Similarity	NPD919	Approved
0.711	Intermediate Similarity	NPD7236	Approved
0.7095	Intermediate Similarity	NPD7819	Suspended
0.7074	Intermediate Similarity	NPD6559	Discontinued
0.7074	Intermediate Similarity	NPD7685	Pre-registration
0.7045	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD7497	Discontinued
0.6994	Remote Similarity	NPD4628	Phase 3
0.6973	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6799	Approved
0.6961	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD8127	Discontinued
0.6957	Remote Similarity	NPD1247	Approved
0.6952	Remote Similarity	NPD3818	Discontinued
0.6932	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3882	Suspended
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5494	Approved
0.6898	Remote Similarity	NPD7473	Discontinued
0.6893	Remote Similarity	NPD6273	Approved
0.6891	Remote Similarity	NPD8150	Discontinued
0.6865	Remote Similarity	NPD7199	Phase 2
0.6854	Remote Similarity	NPD5403	Approved
0.6836	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5401	Approved
0.6833	Remote Similarity	NPD4380	Phase 2
0.6831	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5762	Approved
0.6821	Remote Similarity	NPD5763	Approved
0.6818	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3749	Approved
0.6793	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8407	Phase 2
0.6771	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD1934	Approved
0.6755	Remote Similarity	NPD6166	Phase 2
0.6755	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2532	Approved
0.6742	Remote Similarity	NPD2534	Approved
0.6742	Remote Similarity	NPD2533	Approved
0.674	Remote Similarity	NPD7028	Phase 2
0.6738	Remote Similarity	NPD6232	Discontinued
0.6737	Remote Similarity	NPD5844	Phase 1
0.6724	Remote Similarity	NPD6005	Phase 3
0.6724	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6002	Phase 3
0.6724	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6004	Phase 3
0.6721	Remote Similarity	NPD2801	Approved
0.6719	Remote Similarity	NPD8368	Discontinued
0.6719	Remote Similarity	NPD7251	Discontinued
0.6714	Remote Similarity	NPD7907	Approved
0.6703	Remote Similarity	NPD7411	Suspended
0.6702	Remote Similarity	NPD3926	Phase 2
0.6685	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3226	Approved
0.6684	Remote Similarity	NPD3751	Discontinued
0.6684	Remote Similarity	NPD7808	Phase 3
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7057	Phase 3
0.6649	Remote Similarity	NPD7058	Phase 2
0.6649	Remote Similarity	NPD4965	Approved
0.6649	Remote Similarity	NPD8313	Approved
0.6649	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD8312	Approved
0.6649	Remote Similarity	NPD4966	Approved
0.6649	Remote Similarity	NPD4967	Phase 2
0.6648	Remote Similarity	NPD2800	Approved
0.6648	Remote Similarity	NPD1243	Approved
0.6648	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1471	Phase 3
0.6628	Remote Similarity	NPD6355	Discontinued
0.662	Remote Similarity	NPD4111	Phase 1
0.662	Remote Similarity	NPD4665	Approved
0.6615	Remote Similarity	NPD7472	Approved
0.6615	Remote Similarity	NPD7074	Phase 3
0.6611	Remote Similarity	NPD1512	Approved
0.661	Remote Similarity	NPD3750	Approved
0.6591	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7435	Discontinued
0.6576	Remote Similarity	NPD37	Approved
0.6561	Remote Similarity	NPD3787	Discontinued
0.6556	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2346	Discontinued
0.6532	Remote Similarity	NPD5735	Approved
0.652	Remote Similarity	NPD4107	Approved
0.6514	Remote Similarity	NPD2799	Discontinued
0.6514	Remote Similarity	NPD3748	Approved
0.6514	Remote Similarity	NPD7033	Discontinued
0.651	Remote Similarity	NPD7228	Approved
0.6509	Remote Similarity	NPD5647	Approved
0.6508	Remote Similarity	NPD6959	Discontinued
0.6503	Remote Similarity	NPD7458	Discontinued
0.65	Remote Similarity	NPD1511	Approved
0.6497	Remote Similarity	NPD1549	Phase 2
0.6494	Remote Similarity	NPD6653	Approved
0.6492	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4482	Phase 3
0.6484	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8360	Approved
0.6482	Remote Similarity	NPD8361	Approved
0.6482	Remote Similarity	NPD8435	Approved
0.6477	Remote Similarity	NPD1551	Phase 2
0.6477	Remote Similarity	NPD6099	Approved
0.6477	Remote Similarity	NPD6100	Approved
0.6471	Remote Similarity	NPD7768	Phase 2
0.6456	Remote Similarity	NPD3057	Approved
0.6456	Remote Similarity	NPD2972	Approved
0.6456	Remote Similarity	NPD3533	Approved
0.6453	Remote Similarity	NPD2313	Discontinued
0.6452	Remote Similarity	NPD1465	Phase 2
0.6441	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6782	Approved
0.6439	Remote Similarity	NPD6779	Approved
0.6439	Remote Similarity	NPD6780	Approved
0.6439	Remote Similarity	NPD6776	Approved
0.6439	Remote Similarity	NPD6777	Approved
0.6439	Remote Similarity	NPD6781	Approved
0.6439	Remote Similarity	NPD6778	Approved
0.6425	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1510	Phase 2
0.6412	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD2403	Approved
0.64	Remote Similarity	NPD7048	Phase 3
0.6398	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7874	Approved
0.6389	Remote Similarity	NPD6190	Approved
0.6387	Remote Similarity	NPD7315	Approved
0.6387	Remote Similarity	NPD7229	Phase 3
0.6379	Remote Similarity	NPD4140	Approved
0.6378	Remote Similarity	NPD7240	Approved
0.6377	Remote Similarity	NPD2491	Approved
0.6373	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2344	Approved
0.6346	Remote Similarity	NPD7696	Phase 3
0.6346	Remote Similarity	NPD7697	Approved
0.6346	Remote Similarity	NPD7698	Approved
0.6343	Remote Similarity	NPD447	Suspended
0.6337	Remote Similarity	NPD6832	Phase 2
0.6333	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4110	Phase 3
0.6331	Remote Similarity	NPD7078	Approved
0.6324	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6663	Approved
0.6322	Remote Similarity	NPD8032	Phase 2
0.6319	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8320	Phase 1
0.6316	Remote Similarity	NPD8319	Approved
0.6316	Remote Similarity	NPD7870	Phase 2
0.6316	Remote Similarity	NPD7871	Phase 2
0.6308	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD6353	Approved
0.6307	Remote Similarity	NPD6651	Approved
0.6303	Remote Similarity	NPD7701	Phase 2
0.6302	Remote Similarity	NPD5710	Approved
0.6302	Remote Similarity	NPD5711	Approved
0.6301	Remote Similarity	NPD7095	Approved
0.63	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3448	Approved
0.6293	Remote Similarity	NPD8485	Approved
0.6292	Remote Similarity	NPD2935	Discontinued
0.6291	Remote Similarity	NPD5676	Approved
0.6291	Remote Similarity	NPD7801	Approved
0.6286	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6319	Approved
0.6264	Remote Similarity	NPD6798	Discontinued
0.6264	Remote Similarity	NPD3268	Approved
0.6262	Remote Similarity	NPD8462	Phase 1
0.6257	Remote Similarity	NPD1049	Clinical (unspecified phase)

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