NPASS Compound

Structure

NPC181743 OpenBabel07101719142D 32 36 0 0 1 0 0 0 0 0999 V2000 -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 1.7321 -3.0000 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 -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 -0.0000 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 1.7321 -2.0000 0.0000 C 0 0 1 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 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 -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 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 2 19 1 0 0 0 0 4 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 17 28 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 3 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 6 0 0 0 22 28 1 6 0 0 0 23 30 2 0 0 0 0 24 27 1 1 0 0 0 24 29 1 0 0 0 0 25 31 2 0 0 0 0 25 32 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 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.33
Volume:	485.819
LogP:	6.383
LogD:	5.01
LogS:	-4.498
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.525
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.078
MDCK Permeability:	1.855154914665036e-05
Pgp-inhibitor:	0.93
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	94.46968841552734%
Volume Distribution (VD):	0.841
Pgp-substrate:	1.6361560821533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.456
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.76
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	4.635
Half-life (T1/2):	0.242

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.2
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.333
Skin Sensitization:	0.953
Carcinogencity:	0.423
Eye Corrosion:	0.059
Eye Irritation:	0.116
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC181743

Natural Product ID:	NPC181743
*Common Name:**	Sinocalycanchinensin G
IUPAC Name:	n.a.
Synonyms:	Sinocalycanchinensin G
Standard InCHIKey:	SIWDILYVABWYRB-MBAAMAKOSA-N
Standard InCHI:	InChI=1S/C29H44O3/c1-18(7-6-8-19(2)25(31)32)21-11-13-27(5)24-10-9-22-20(3)23(30)12-14-28(22)17-29(24,28)16-15-26(21,27)4/h8,18,20-22,24H,6-7,9-17H2,1-5H3,(H,31,32)/b19-8-/t18-,20+,21-,22+,24+,26-,27+,28-,29+/m1/s1
SMILES:	C[C@H](CC/C=C(/C)C(=O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)C(=O)CC[C@]54C[C@@]35CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774191
PubChem CID:	52952952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
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	=	19.9	ug.mL-1	PMID[521332]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23.7	ug.mL-1	PMID[521332]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	7.3	ug.mL-1	PMID[521332]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	14.8	ug.mL-1	PMID[521332]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21.6	ug.mL-1	PMID[521332]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21.4	ug.mL-1	PMID[521332]

☑ 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 NPC181743 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	161
0.1-0.2	1532
0.2-0.3	7806
0.3-0.4	15211
0.4-0.5	7328
0.5-0.6	6671
0.6-0.7	3407
0.7-0.8	507
0.8-0.85	50
0.85-0.9	15
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC178025
1.0	High Similarity	NPC16287
0.9873	High Similarity	NPC60350
0.963	High Similarity	NPC476293
0.9494	High Similarity	NPC472239
0.925	High Similarity	NPC472867
0.925	High Similarity	NPC142253
0.925	High Similarity	NPC3511
0.9176	High Similarity	NPC23217
0.9024	High Similarity	NPC87552
0.8916	High Similarity	NPC8571
0.8902	High Similarity	NPC3856
0.8902	High Similarity	NPC279639
0.8864	High Similarity	NPC476174
0.8824	High Similarity	NPC117122
0.881	High Similarity	NPC186975
0.878	High Similarity	NPC469799
0.878	High Similarity	NPC469806
0.878	High Similarity	NPC469805
0.878	High Similarity	NPC469804
0.8764	High Similarity	NPC29152
0.8706	High Similarity	NPC236618
0.8667	High Similarity	NPC156546
0.8625	High Similarity	NPC91665
0.8608	High Similarity	NPC469803
0.8608	High Similarity	NPC255650
0.8554	High Similarity	NPC320514
0.8537	High Similarity	NPC469798
0.8537	High Similarity	NPC469797
0.8506	High Similarity	NPC66344
0.8506	High Similarity	NPC262043
0.85	High Similarity	NPC69408
0.8488	Intermediate Similarity	NPC136948
0.8481	Intermediate Similarity	NPC255021
0.8471	Intermediate Similarity	NPC29447
0.8462	Intermediate Similarity	NPC133253
0.8462	Intermediate Similarity	NPC21944
0.8375	Intermediate Similarity	NPC476346
0.8372	Intermediate Similarity	NPC472869
0.8354	Intermediate Similarity	NPC130016
0.8354	Intermediate Similarity	NPC109576
0.8354	Intermediate Similarity	NPC303613
0.8354	Intermediate Similarity	NPC180015
0.8354	Intermediate Similarity	NPC56747
0.8354	Intermediate Similarity	NPC474228
0.8353	Intermediate Similarity	NPC248758
0.8353	Intermediate Similarity	NPC19849
0.8353	Intermediate Similarity	NPC164577
0.8353	Intermediate Similarity	NPC472864
0.8333	Intermediate Similarity	NPC214770
0.8333	Intermediate Similarity	NPC477856
0.8315	Intermediate Similarity	NPC470113
0.8235	Intermediate Similarity	NPC472740
0.8235	Intermediate Similarity	NPC41539
0.8235	Intermediate Similarity	NPC97913
0.8214	Intermediate Similarity	NPC147066
0.8214	Intermediate Similarity	NPC477372
0.8205	Intermediate Similarity	NPC477857
0.8193	Intermediate Similarity	NPC158846
0.8182	Intermediate Similarity	NPC472870
0.8148	Intermediate Similarity	NPC293803
0.814	Intermediate Similarity	NPC476038
0.814	Intermediate Similarity	NPC472865
0.814	Intermediate Similarity	NPC194937
0.8125	Intermediate Similarity	NPC251705
0.8111	Intermediate Similarity	NPC110923
0.8111	Intermediate Similarity	NPC476187
0.8111	Intermediate Similarity	NPC473986
0.8111	Intermediate Similarity	NPC204341
0.8111	Intermediate Similarity	NPC474018
0.8111	Intermediate Similarity	NPC74296
0.8101	Intermediate Similarity	NPC35734
0.8101	Intermediate Similarity	NPC265782
0.8101	Intermediate Similarity	NPC251929
0.8101	Intermediate Similarity	NPC282593
0.8101	Intermediate Similarity	NPC2634
0.8101	Intermediate Similarity	NPC159577
0.8101	Intermediate Similarity	NPC307176
0.8046	Intermediate Similarity	NPC472940
0.8046	Intermediate Similarity	NPC472931
0.8046	Intermediate Similarity	NPC269638
0.8046	Intermediate Similarity	NPC283733
0.8046	Intermediate Similarity	NPC11711
0.8043	Intermediate Similarity	NPC293052
0.8025	Intermediate Similarity	NPC309852
0.8023	Intermediate Similarity	NPC474976
0.8023	Intermediate Similarity	NPC474790
0.8023	Intermediate Similarity	NPC470015
0.8023	Intermediate Similarity	NPC168188
0.8022	Intermediate Similarity	NPC476304
0.8	Intermediate Similarity	NPC471898
0.8	Intermediate Similarity	NPC115023
0.8	Intermediate Similarity	NPC201912
0.8	Intermediate Similarity	NPC305501
0.8	Intermediate Similarity	NPC472866
0.8	Intermediate Similarity	NPC4166
0.8	Intermediate Similarity	NPC234707
0.8	Intermediate Similarity	NPC38350
0.8	Intermediate Similarity	NPC278459
0.8	Intermediate Similarity	NPC54123
0.7979	Intermediate Similarity	NPC98868
0.7976	Intermediate Similarity	NPC215843
0.7976	Intermediate Similarity	NPC190211
0.7976	Intermediate Similarity	NPC477371
0.7975	Intermediate Similarity	NPC139397
0.7957	Intermediate Similarity	NPC472941
0.7957	Intermediate Similarity	NPC456
0.7955	Intermediate Similarity	NPC70661
0.7952	Intermediate Similarity	NPC212661
0.7952	Intermediate Similarity	NPC471035
0.7935	Intermediate Similarity	NPC476186
0.7907	Intermediate Similarity	NPC260956
0.7907	Intermediate Similarity	NPC311092
0.7901	Intermediate Similarity	NPC470044
0.7901	Intermediate Similarity	NPC470045
0.7889	Intermediate Similarity	NPC473999
0.7889	Intermediate Similarity	NPC309603
0.7882	Intermediate Similarity	NPC474509
0.7875	Intermediate Similarity	NPC260040
0.7875	Intermediate Similarity	NPC40574
0.7865	Intermediate Similarity	NPC75315
0.7865	Intermediate Similarity	NPC163016
0.7865	Intermediate Similarity	NPC476409
0.7865	Intermediate Similarity	NPC128644
0.7865	Intermediate Similarity	NPC93778
0.7857	Intermediate Similarity	NPC198240
0.7857	Intermediate Similarity	NPC105197
0.7857	Intermediate Similarity	NPC82635
0.7848	Intermediate Similarity	NPC20610
0.7841	Intermediate Similarity	NPC94531
0.7841	Intermediate Similarity	NPC474537
0.7841	Intermediate Similarity	NPC311702
0.7841	Intermediate Similarity	NPC471224
0.7841	Intermediate Similarity	NPC123319
0.7831	Intermediate Similarity	NPC20466
0.7831	Intermediate Similarity	NPC19907
0.7831	Intermediate Similarity	NPC474463
0.7826	Intermediate Similarity	NPC474736
0.7826	Intermediate Similarity	NPC472871
0.7821	Intermediate Similarity	NPC39462
0.7821	Intermediate Similarity	NPC189917
0.7821	Intermediate Similarity	NPC107704
0.7821	Intermediate Similarity	NPC96812
0.7821	Intermediate Similarity	NPC168824
0.7816	Intermediate Similarity	NPC69279
0.7816	Intermediate Similarity	NPC83569
0.7816	Intermediate Similarity	NPC49019
0.7816	Intermediate Similarity	NPC215893
0.7816	Intermediate Similarity	NPC167103
0.7805	Intermediate Similarity	NPC474796
0.7805	Intermediate Similarity	NPC329866
0.7805	Intermediate Similarity	NPC474797
0.7805	Intermediate Similarity	NPC20025
0.7802	Intermediate Similarity	NPC48010
0.7789	Intermediate Similarity	NPC235464
0.7789	Intermediate Similarity	NPC197386
0.7789	Intermediate Similarity	NPC166745
0.7778	Intermediate Similarity	NPC48107
0.7778	Intermediate Similarity	NPC5701
0.7766	Intermediate Similarity	NPC301534
0.7766	Intermediate Similarity	NPC250757
0.7766	Intermediate Similarity	NPC195366
0.7766	Intermediate Similarity	NPC114743
0.7765	Intermediate Similarity	NPC192744
0.775	Intermediate Similarity	NPC182815
0.7742	Intermediate Similarity	NPC124207
0.7738	Intermediate Similarity	NPC97377
0.7738	Intermediate Similarity	NPC165711
0.7738	Intermediate Similarity	NPC61952
0.7738	Intermediate Similarity	NPC470557
0.7738	Intermediate Similarity	NPC66105
0.7727	Intermediate Similarity	NPC165064
0.7727	Intermediate Similarity	NPC96095
0.7727	Intermediate Similarity	NPC214043
0.7727	Intermediate Similarity	NPC85774
0.7717	Intermediate Similarity	NPC473998
0.7717	Intermediate Similarity	NPC475806
0.7711	Intermediate Similarity	NPC65650
0.7708	Intermediate Similarity	NPC287833
0.7708	Intermediate Similarity	NPC201406
0.7708	Intermediate Similarity	NPC470074
0.7701	Intermediate Similarity	NPC193347
0.7701	Intermediate Similarity	NPC133391
0.7701	Intermediate Similarity	NPC477858
0.7701	Intermediate Similarity	NPC100297
0.7692	Intermediate Similarity	NPC214387
0.7692	Intermediate Similarity	NPC107258
0.7692	Intermediate Similarity	NPC146554
0.7692	Intermediate Similarity	NPC285982
0.7692	Intermediate Similarity	NPC472240
0.7692	Intermediate Similarity	NPC474844
0.7692	Intermediate Similarity	NPC262858
0.7684	Intermediate Similarity	NPC476253
0.7684	Intermediate Similarity	NPC253826
0.7674	Intermediate Similarity	NPC472478
0.7667	Intermediate Similarity	NPC96496
0.766	Intermediate Similarity	NPC84383
0.766	Intermediate Similarity	NPC318282
0.766	Intermediate Similarity	NPC173875
0.766	Intermediate Similarity	NPC174948

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 NPC181743 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	1721
0.2-0.3	4421
0.3-0.4	2037
0.4-0.5	423
0.5-0.6	173
0.6-0.7	173
0.7-0.8	54
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
0.8101	Intermediate Similarity	NPD4691	Approved
0.8101	Intermediate Similarity	NPD4747	Approved
0.7975	Intermediate Similarity	NPD4137	Phase 3
0.7805	Intermediate Similarity	NPD4058	Approved
0.7805	Intermediate Similarity	NPD5733	Approved
0.7701	Intermediate Similarity	NPD4221	Approved
0.7701	Intermediate Similarity	NPD4223	Phase 3
0.764	Intermediate Similarity	NPD5329	Approved
0.759	Intermediate Similarity	NPD4687	Approved
0.7561	Intermediate Similarity	NPD5276	Approved
0.7528	Intermediate Similarity	NPD4197	Approved
0.7407	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5737	Approved
0.7391	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6672	Approved
0.7363	Intermediate Similarity	NPD4690	Approved
0.7363	Intermediate Similarity	NPD4689	Approved
0.7363	Intermediate Similarity	NPD6684	Approved
0.7363	Intermediate Similarity	NPD4623	Approved
0.7363	Intermediate Similarity	NPD7146	Approved
0.7363	Intermediate Similarity	NPD5205	Approved
0.7363	Intermediate Similarity	NPD4519	Discontinued
0.7363	Intermediate Similarity	NPD5330	Approved
0.7363	Intermediate Similarity	NPD7521	Approved
0.7363	Intermediate Similarity	NPD7334	Approved
0.7363	Intermediate Similarity	NPD4693	Phase 3
0.7363	Intermediate Similarity	NPD4138	Approved
0.7363	Intermediate Similarity	NPD4688	Approved
0.7363	Intermediate Similarity	NPD5690	Phase 2
0.7363	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD6404	Discontinued
0.734	Intermediate Similarity	NPD6079	Approved
0.734	Intermediate Similarity	NPD5284	Approved
0.734	Intermediate Similarity	NPD5281	Approved
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD4786	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD3666	Approved
0.732	Intermediate Similarity	NPD6084	Phase 2
0.732	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD5328	Approved
0.7312	Intermediate Similarity	NPD6904	Approved
0.7312	Intermediate Similarity	NPD6080	Approved
0.7312	Intermediate Similarity	NPD6673	Approved
0.7292	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6399	Phase 3
0.7241	Intermediate Similarity	NPD3617	Approved
0.7241	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4788	Approved
0.7204	Intermediate Similarity	NPD6903	Approved
0.7204	Intermediate Similarity	NPD5208	Approved
0.7188	Intermediate Similarity	NPD6001	Approved
0.7174	Intermediate Similarity	NPD3618	Phase 1
0.7174	Intermediate Similarity	NPD4694	Approved
0.7174	Intermediate Similarity	NPD6098	Approved
0.7174	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5280	Approved
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7159	Intermediate Similarity	NPD4195	Approved
0.7158	Intermediate Similarity	NPD7515	Phase 2
0.7158	Intermediate Similarity	NPD5693	Phase 1
0.7128	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4753	Phase 2
0.7113	Intermediate Similarity	NPD5695	Phase 3
0.7111	Intermediate Similarity	NPD3667	Approved
0.7079	Intermediate Similarity	NPD4695	Discontinued
0.7071	Intermediate Similarity	NPD5696	Approved
0.7071	Intermediate Similarity	NPD7638	Approved
0.7065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7748	Approved
0.6989	Remote Similarity	NPD5279	Phase 3
0.6979	Remote Similarity	NPD6050	Approved
0.6972	Remote Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4202	Approved
0.6907	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD5207	Approved
0.6875	Remote Similarity	NPD5692	Phase 3
0.6869	Remote Similarity	NPD5221	Approved
0.6869	Remote Similarity	NPD7614	Phase 1
0.6869	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5222	Approved
0.6863	Remote Similarity	NPD5211	Phase 2
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6848	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7128	Approved
0.6827	Remote Similarity	NPD5739	Approved
0.6827	Remote Similarity	NPD6675	Approved
0.6827	Remote Similarity	NPD6402	Approved
0.6813	Remote Similarity	NPD8028	Phase 2
0.6804	Remote Similarity	NPD5694	Approved
0.68	Remote Similarity	NPD7902	Approved
0.68	Remote Similarity	NPD5173	Approved
0.6762	Remote Similarity	NPD5697	Approved
0.6747	Remote Similarity	NPD4224	Phase 2
0.6744	Remote Similarity	NPD6081	Approved
0.6737	Remote Similarity	NPD3573	Approved
0.6731	Remote Similarity	NPD5141	Approved
0.6729	Remote Similarity	NPD7102	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6702	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD4096	Approved
0.6701	Remote Similarity	NPD5785	Approved
0.67	Remote Similarity	NPD4697	Phase 3
0.6698	Remote Similarity	NPD7320	Approved
0.6698	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6634	Remote Similarity	NPD4755	Approved
0.6634	Remote Similarity	NPD5959	Approved
0.6633	Remote Similarity	NPD7637	Suspended
0.6633	Remote Similarity	NPD8035	Phase 2
0.6633	Remote Similarity	NPD8034	Phase 2
0.663	Remote Similarity	NPD4139	Approved
0.663	Remote Similarity	NPD4692	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6604	Remote Similarity	NPD5701	Approved
0.6602	Remote Similarity	NPD5223	Approved
0.6596	Remote Similarity	NPD3668	Phase 3
0.6552	Remote Similarity	NPD4243	Approved
0.6538	Remote Similarity	NPD5091	Approved
0.6538	Remote Similarity	NPD5224	Approved
0.6538	Remote Similarity	NPD5226	Approved
0.6538	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD7632	Discontinued
0.6514	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4700	Approved
0.65	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7900	Approved
0.6495	Remote Similarity	NPD4518	Approved
0.6489	Remote Similarity	NPD5362	Discontinued
0.6476	Remote Similarity	NPD6052	Approved
0.6476	Remote Similarity	NPD5175	Approved
0.6476	Remote Similarity	NPD5174	Approved
0.6463	Remote Similarity	NPD4193	Approved
0.6463	Remote Similarity	NPD4191	Approved
0.6463	Remote Similarity	NPD4194	Approved
0.6463	Remote Similarity	NPD4192	Approved
0.6452	Remote Similarity	NPD6902	Approved
0.6449	Remote Similarity	NPD6614	Approved
0.6436	Remote Similarity	NPD5654	Approved
0.6429	Remote Similarity	NPD6868	Approved
0.6404	Remote Similarity	NPD4785	Approved
0.6404	Remote Similarity	NPD4784	Approved
0.6404	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4632	Approved
0.6395	Remote Similarity	NPD5360	Phase 3
0.6395	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6686	Approved
0.6383	Remote Similarity	NPD4269	Approved
0.6383	Remote Similarity	NPD4270	Approved
0.6373	Remote Similarity	NPD7732	Phase 3
0.6355	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD1696	Phase 3
0.6354	Remote Similarity	NPD1694	Approved
0.6344	Remote Similarity	NPD4252	Approved
0.6344	Remote Similarity	NPD7525	Registered
0.6333	Remote Similarity	NPD6942	Approved
0.6333	Remote Similarity	NPD7339	Approved
0.6325	Remote Similarity	NPD7604	Phase 2
0.6321	Remote Similarity	NPD4754	Approved
0.6316	Remote Similarity	NPD6335	Approved
0.6296	Remote Similarity	NPD287	Approved
0.6296	Remote Similarity	NPD6412	Phase 2
0.6283	Remote Similarity	NPD6274	Approved
0.6264	Remote Similarity	NPD6117	Approved
0.6263	Remote Similarity	NPD6051	Approved
0.6261	Remote Similarity	NPD7100	Approved
0.6261	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD4789	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD5168	Approved
0.6228	Remote Similarity	NPD6317	Approved
0.6228	Remote Similarity	NPD6009	Approved
0.6204	Remote Similarity	NPD4768	Approved
0.6204	Remote Similarity	NPD4767	Approved
0.6196	Remote Similarity	NPD6116	Phase 1

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