NPASS Compound

Structure

NPC236618 OpenBabel07101719142D 33 36 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5446 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 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 -0.8660 1.5000 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 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2063 6.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9192 5.1132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 3 20 1 0 0 0 0 4 26 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 2 1 1 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 6 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 27 1 6 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.32
Volume:	500.529
LogP:	5.865
LogD:	4.156
LogS:	-3.724
# Rotatable Bonds:	9
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	5.543
Fsp3:	0.793
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:	-5.792
MDCK Permeability:	4.581924713420449e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	97.45027923583984%
Volume Distribution (VD):	0.573
Pgp-substrate:	3.4129295349121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.535
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	1.168
Half-life (T1/2):	0.621

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.489
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.178
Maximum Recommended Daily Dose:	0.599
Skin Sensitization:	0.932
Carcinogencity:	0.451
Eye Corrosion:	0.042
Eye Irritation:	0.094
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC236618

Natural Product ID:	NPC236618
*Common Name:**	Sinocalycanchinensin A
IUPAC Name:	n.a.
Synonyms:	Sinocalycanchinensin A
Standard InCHIKey:	SIWZGYBIFDMURY-MLWVRJGVSA-N
Standard InCHI:	InChI=1S/C29H44O4/c1-6-21-10-11-23-27(5)14-12-22(19(2)8-7-9-20(3)25(32)33)26(27,4)16-17-29(23)18-28(21,29)15-13-24(30)31/h6,9,19,21-23H,1,7-8,10-18H2,2-5H3,(H,30,31)(H,32,33)/b20-9-/t19-,21-,22-,23+,26-,27+,28-,29+/m1/s1
SMILES:	C=C[C@@H]1CC[C@H]2[C@]3(C)CC[C@H]([C@H](C)CC/C=C(/C)C(=O)O)[C@@]3(C)CC[C@@]32C[C@]13CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774185
PubChem CID:	54584284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33379	sinocalycanthus chinensis	Species	n.a.	n.a.	leaves	n.a.	n.a.	PMID[21493075]

☑ 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	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	30.7	ug.mL-1	PMID[475299]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	61.6	ug.mL-1	PMID[475299]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	38.9	ug.mL-1	PMID[475299]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	29.9	ug.mL-1	PMID[475299]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30.4	ug.mL-1	PMID[475299]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33.4	ug.mL-1	PMID[475299]

☑ 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 NPC236618 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	164
0.1-0.2	1093
0.2-0.3	5148
0.3-0.4	15167
0.4-0.5	8026
0.5-0.6	7275
0.6-0.7	4581
0.7-0.8	1126
0.8-0.85	74
0.85-0.9	28
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC186975
0.9759	High Similarity	NPC66344
0.9639	High Similarity	NPC117122
0.939	High Similarity	NPC164577
0.939	High Similarity	NPC19849
0.939	High Similarity	NPC472864
0.9302	High Similarity	NPC470113
0.9268	High Similarity	NPC97913
0.9205	High Similarity	NPC293052
0.9167	High Similarity	NPC472869
0.9157	High Similarity	NPC472865
0.908	High Similarity	NPC476187
0.907	High Similarity	NPC262043
0.9048	High Similarity	NPC269638
0.9012	High Similarity	NPC158846
0.8989	High Similarity	NPC476174
0.8953	High Similarity	NPC472870
0.8929	High Similarity	NPC248758
0.8929	High Similarity	NPC194937
0.8929	High Similarity	NPC476038
0.8889	High Similarity	NPC198240
0.8889	High Similarity	NPC29152
0.8864	High Similarity	NPC473986
0.8864	High Similarity	NPC474018
0.8837	High Similarity	NPC136948
0.8837	High Similarity	NPC128644
0.8824	High Similarity	NPC60350
0.8824	High Similarity	NPC283733
0.8824	High Similarity	NPC29447
0.8791	High Similarity	NPC156546
0.8765	High Similarity	NPC61952
0.875	High Similarity	NPC472866
0.8706	High Similarity	NPC178025
0.8706	High Similarity	NPC181743
0.8706	High Similarity	NPC16287
0.8696	High Similarity	NPC98868
0.8652	High Similarity	NPC204341
0.8621	High Similarity	NPC476293
0.8588	High Similarity	NPC167103
0.8588	High Similarity	NPC279639
0.8588	High Similarity	NPC3856
0.8571	High Similarity	NPC477372
0.8556	High Similarity	NPC472871
0.8478	Intermediate Similarity	NPC250757
0.8478	Intermediate Similarity	NPC301534
0.8471	Intermediate Similarity	NPC469804
0.8471	Intermediate Similarity	NPC469805
0.8471	Intermediate Similarity	NPC472239
0.8471	Intermediate Similarity	NPC469806
0.8471	Intermediate Similarity	NPC320514
0.8471	Intermediate Similarity	NPC469799
0.8404	Intermediate Similarity	NPC470074
0.837	Intermediate Similarity	NPC33473
0.8353	Intermediate Similarity	NPC147066
0.8353	Intermediate Similarity	NPC40228
0.8353	Intermediate Similarity	NPC278459
0.8352	Intermediate Similarity	NPC476304
0.8333	Intermediate Similarity	NPC477371
0.8316	Intermediate Similarity	NPC118174
0.8293	Intermediate Similarity	NPC472327
0.8293	Intermediate Similarity	NPC476795
0.828	Intermediate Similarity	NPC456
0.828	Intermediate Similarity	NPC472941
0.8276	Intermediate Similarity	NPC165064
0.8261	Intermediate Similarity	NPC124207
0.8261	Intermediate Similarity	NPC476186
0.8256	Intermediate Similarity	NPC142253
0.8256	Intermediate Similarity	NPC133391
0.8256	Intermediate Similarity	NPC472867
0.8256	Intermediate Similarity	NPC3511
0.8242	Intermediate Similarity	NPC110923
0.8242	Intermediate Similarity	NPC74296
0.8242	Intermediate Similarity	NPC23217
0.8235	Intermediate Similarity	NPC469797
0.8235	Intermediate Similarity	NPC469798
0.8222	Intermediate Similarity	NPC310236
0.8222	Intermediate Similarity	NPC128496
0.8222	Intermediate Similarity	NPC174342
0.8222	Intermediate Similarity	NPC214387
0.8214	Intermediate Similarity	NPC179028
0.8214	Intermediate Similarity	NPC321690
0.8214	Intermediate Similarity	NPC239098
0.8202	Intermediate Similarity	NPC476409
0.8193	Intermediate Similarity	NPC20466
0.8193	Intermediate Similarity	NPC246445
0.8182	Intermediate Similarity	NPC8571
0.8182	Intermediate Similarity	NPC142649
0.8182	Intermediate Similarity	NPC65661
0.8172	Intermediate Similarity	NPC171395
0.8161	Intermediate Similarity	NPC168188
0.8161	Intermediate Similarity	NPC215893
0.8161	Intermediate Similarity	NPC470015
0.8161	Intermediate Similarity	NPC310470
0.8161	Intermediate Similarity	NPC49019
0.8161	Intermediate Similarity	NPC477373
0.8161	Intermediate Similarity	NPC472740
0.8152	Intermediate Similarity	NPC474736
0.8144	Intermediate Similarity	NPC476237
0.814	Intermediate Similarity	NPC201912
0.814	Intermediate Similarity	NPC38350
0.8132	Intermediate Similarity	NPC477149
0.8132	Intermediate Similarity	NPC477147
0.8125	Intermediate Similarity	NPC224720
0.8125	Intermediate Similarity	NPC476240
0.8125	Intermediate Similarity	NPC476223
0.8125	Intermediate Similarity	NPC282524
0.8118	Intermediate Similarity	NPC274996
0.8118	Intermediate Similarity	NPC196827
0.8111	Intermediate Similarity	NPC193843
0.8111	Intermediate Similarity	NPC104560
0.8111	Intermediate Similarity	NPC48107
0.8111	Intermediate Similarity	NPC249889
0.8105	Intermediate Similarity	NPC235464
0.8105	Intermediate Similarity	NPC57079
0.8105	Intermediate Similarity	NPC108368
0.8105	Intermediate Similarity	NPC197386
0.8105	Intermediate Similarity	NPC166745
0.8095	Intermediate Similarity	NPC97377
0.809	Intermediate Similarity	NPC70661
0.809	Intermediate Similarity	NPC475007
0.8085	Intermediate Similarity	NPC195366
0.8085	Intermediate Similarity	NPC114743
0.8072	Intermediate Similarity	NPC469803
0.8072	Intermediate Similarity	NPC476844
0.8072	Intermediate Similarity	NPC279666
0.8072	Intermediate Similarity	NPC192540
0.8068	Intermediate Similarity	NPC87552
0.8065	Intermediate Similarity	NPC8993
0.8065	Intermediate Similarity	NPC299100
0.8049	Intermediate Similarity	NPC35656
0.8046	Intermediate Similarity	NPC100297
0.8046	Intermediate Similarity	NPC260956
0.8043	Intermediate Similarity	NPC475806
0.8043	Intermediate Similarity	NPC473998
0.8025	Intermediate Similarity	NPC235586
0.8022	Intermediate Similarity	NPC473999
0.8022	Intermediate Similarity	NPC262858
0.8022	Intermediate Similarity	NPC472240
0.8022	Intermediate Similarity	NPC146554
0.8022	Intermediate Similarity	NPC309603
0.8021	Intermediate Similarity	NPC287833
0.8021	Intermediate Similarity	NPC476303
0.8021	Intermediate Similarity	NPC266955
0.8021	Intermediate Similarity	NPC476274
0.8	Intermediate Similarity	NPC476253
0.8	Intermediate Similarity	NPC260385
0.8	Intermediate Similarity	NPC59436
0.8	Intermediate Similarity	NPC275494
0.8	Intermediate Similarity	NPC110094
0.8	Intermediate Similarity	NPC280654
0.8	Intermediate Similarity	NPC253826
0.8	Intermediate Similarity	NPC93778
0.8	Intermediate Similarity	NPC169095
0.8	Intermediate Similarity	NPC471409
0.8	Intermediate Similarity	NPC108078
0.8	Intermediate Similarity	NPC107243
0.8	Intermediate Similarity	NPC74410
0.8	Intermediate Similarity	NPC96496
0.7979	Intermediate Similarity	NPC174948
0.7979	Intermediate Similarity	NPC84383
0.7979	Intermediate Similarity	NPC173875
0.7979	Intermediate Similarity	NPC318282
0.7979	Intermediate Similarity	NPC180950
0.7979	Intermediate Similarity	NPC469995
0.7978	Intermediate Similarity	NPC474537
0.7978	Intermediate Similarity	NPC471224
0.7978	Intermediate Similarity	NPC86316
0.7978	Intermediate Similarity	NPC311702
0.7978	Intermediate Similarity	NPC123319
0.7978	Intermediate Similarity	NPC106416
0.7978	Intermediate Similarity	NPC94531
0.7976	Intermediate Similarity	NPC180886
0.7976	Intermediate Similarity	NPC69143
0.7959	Intermediate Similarity	NPC72151
0.7959	Intermediate Similarity	NPC176883
0.7957	Intermediate Similarity	NPC151722
0.7957	Intermediate Similarity	NPC38232
0.7955	Intermediate Similarity	NPC83569
0.7955	Intermediate Similarity	NPC477852
0.7955	Intermediate Similarity	NPC69279
0.7952	Intermediate Similarity	NPC251970
0.7952	Intermediate Similarity	NPC237591
0.7952	Intermediate Similarity	NPC476046
0.7952	Intermediate Similarity	NPC103958
0.7952	Intermediate Similarity	NPC241854
0.7952	Intermediate Similarity	NPC3753
0.7952	Intermediate Similarity	NPC46610
0.7952	Intermediate Similarity	NPC18819
0.7952	Intermediate Similarity	NPC161923
0.7952	Intermediate Similarity	NPC283908
0.7952	Intermediate Similarity	NPC183503
0.7938	Intermediate Similarity	NPC472924
0.7938	Intermediate Similarity	NPC115899
0.7938	Intermediate Similarity	NPC99411
0.7935	Intermediate Similarity	NPC48010
0.7931	Intermediate Similarity	NPC229584
0.7931	Intermediate Similarity	NPC90055
0.7931	Intermediate Similarity	NPC471898
0.7931	Intermediate Similarity	NPC14203
0.7927	Intermediate Similarity	NPC160817

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 NPC236618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1378
0.2-0.3	3920
0.3-0.4	2561
0.4-0.5	671
0.5-0.6	194
0.6-0.7	170
0.7-0.8	108
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
0.7849	Intermediate Similarity	NPD5281	Approved
0.7849	Intermediate Similarity	NPD5284	Approved
0.7841	Intermediate Similarity	NPD4221	Approved
0.7841	Intermediate Similarity	NPD4223	Phase 3
0.7841	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD6404	Discontinued
0.7778	Intermediate Similarity	NPD5329	Approved
0.7717	Intermediate Similarity	NPD6672	Approved
0.7717	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD5690	Phase 2
0.7692	Intermediate Similarity	NPD4623	Approved
0.7692	Intermediate Similarity	NPD4519	Discontinued
0.7667	Intermediate Similarity	NPD4197	Approved
0.766	Intermediate Similarity	NPD6079	Approved
0.7634	Intermediate Similarity	NPD6904	Approved
0.7634	Intermediate Similarity	NPD6673	Approved
0.7634	Intermediate Similarity	NPD6080	Approved
0.7629	Intermediate Similarity	NPD6084	Phase 2
0.7629	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7474	Intermediate Similarity	NPD5693	Phase 1
0.7473	Intermediate Similarity	NPD3666	Approved
0.7473	Intermediate Similarity	NPD4786	Approved
0.7473	Intermediate Similarity	NPD3665	Phase 1
0.7473	Intermediate Similarity	NPD3133	Approved
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD4753	Phase 2
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7423	Intermediate Similarity	NPD5695	Phase 3
0.7416	Intermediate Similarity	NPD4695	Discontinued
0.7407	Intermediate Similarity	NPD7115	Discovery
0.7386	Intermediate Similarity	NPD3617	Approved
0.7374	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD5696	Approved
0.7347	Intermediate Similarity	NPD5221	Approved
0.7347	Intermediate Similarity	NPD5222	Approved
0.7347	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5208	Approved
0.734	Intermediate Similarity	NPD6903	Approved
0.734	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5211	Phase 2
0.732	Intermediate Similarity	NPD6001	Approved
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7312	Intermediate Similarity	NPD4694	Approved
0.7312	Intermediate Similarity	NPD6098	Approved
0.7312	Intermediate Similarity	NPD5280	Approved
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7292	Intermediate Similarity	NPD6050	Approved
0.7292	Intermediate Similarity	NPD7515	Phase 2
0.7292	Intermediate Similarity	NPD5694	Approved
0.7273	Intermediate Similarity	NPD5173	Approved
0.7263	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD3667	Approved
0.7212	Intermediate Similarity	NPD5697	Approved
0.7204	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5363	Approved
0.7188	Intermediate Similarity	NPD5692	Phase 3
0.7188	Intermediate Similarity	NPD5785	Approved
0.7188	Intermediate Similarity	NPD5207	Approved
0.7184	Intermediate Similarity	NPD5141	Approved
0.7176	Intermediate Similarity	NPD4747	Approved
0.7176	Intermediate Similarity	NPD4691	Approved
0.7174	Intermediate Similarity	NPD4788	Approved
0.7174	Intermediate Similarity	NPD5362	Discontinued
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7129	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7126	Intermediate Similarity	NPD4058	Approved
0.7115	Intermediate Similarity	NPD5739	Approved
0.7115	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD6402	Approved
0.7115	Intermediate Similarity	NPD7128	Approved
0.7113	Intermediate Similarity	NPD7637	Suspended
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD4137	Phase 3
0.7053	Intermediate Similarity	NPD3573	Approved
0.7041	Intermediate Similarity	NPD5133	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.7037	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD7614	Phase 1
0.7	Intermediate Similarity	NPD4697	Phase 3
0.699	Remote Similarity	NPD5226	Approved
0.699	Remote Similarity	NPD5225	Approved
0.699	Remote Similarity	NPD5091	Approved
0.699	Remote Similarity	NPD4633	Approved
0.699	Remote Similarity	NPD5224	Approved
0.6981	Remote Similarity	NPD7320	Approved
0.6939	Remote Similarity	NPD8035	Phase 2
0.6939	Remote Similarity	NPD8034	Phase 2
0.6932	Remote Similarity	NPD4687	Approved
0.6932	Remote Similarity	NPD5733	Approved
0.6932	Remote Similarity	NPD4785	Approved
0.6932	Remote Similarity	NPD4784	Approved
0.6931	Remote Similarity	NPD7902	Approved
0.6931	Remote Similarity	NPD4755	Approved
0.6931	Remote Similarity	NPD5959	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6916	Remote Similarity	NPD6373	Approved
0.6916	Remote Similarity	NPD6372	Approved
0.6915	Remote Similarity	NPD3668	Phase 3
0.6897	Remote Similarity	NPD4243	Approved
0.6897	Remote Similarity	NPD6081	Approved
0.6887	Remote Similarity	NPD6614	Approved
0.6887	Remote Similarity	NPD5701	Approved
0.6882	Remote Similarity	NPD4270	Approved
0.6882	Remote Similarity	NPD4269	Approved
0.6863	Remote Similarity	NPD4225	Approved
0.6847	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD1694	Approved
0.6837	Remote Similarity	NPD4096	Approved
0.6827	Remote Similarity	NPD7632	Discontinued
0.6822	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD4632	Approved
0.6809	Remote Similarity	NPD5332	Approved
0.6809	Remote Similarity	NPD5331	Approved
0.6804	Remote Similarity	NPD4518	Approved
0.6796	Remote Similarity	NPD4700	Approved
0.6789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4790	Discontinued
0.6774	Remote Similarity	NPD4139	Approved
0.6774	Remote Similarity	NPD4692	Approved
0.6774	Remote Similarity	NPD6902	Approved
0.6762	Remote Similarity	NPD6052	Approved
0.6735	Remote Similarity	NPD6051	Approved
0.6733	Remote Similarity	NPD5654	Approved
0.6726	Remote Similarity	NPD6335	Approved
0.6724	Remote Similarity	NPD7604	Phase 2
0.6706	Remote Similarity	NPD4224	Phase 2
0.6705	Remote Similarity	NPD5276	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6637	Remote Similarity	NPD6317	Approved
0.6637	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6634	Remote Similarity	NPD7900	Approved
0.6634	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7154	Phase 3
0.663	Remote Similarity	NPD4268	Approved
0.663	Remote Similarity	NPD4271	Approved
0.6604	Remote Similarity	NPD4754	Approved
0.6598	Remote Similarity	NPD5786	Approved
0.6593	Remote Similarity	NPD6117	Approved
0.6579	Remote Similarity	NPD6314	Approved
0.6579	Remote Similarity	NPD6313	Approved
0.6574	Remote Similarity	NPD6412	Phase 2
0.6559	Remote Similarity	NPD6929	Approved
0.6556	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6926	Approved
0.6556	Remote Similarity	NPD6924	Approved
0.6552	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6274	Approved
0.6545	Remote Similarity	NPD5169	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