NPASS Compound

Structure

NPC474844 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 2.3164 1.2784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2509 0.6546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4399 -2.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9399 -1.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8418 -3.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2485 -0.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6036 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5738 -1.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5738 -4.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7078 -0.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7078 -3.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8907 -2.6576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5817 -0.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3030 -1.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5738 -2.3486 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8418 -2.3486 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4399 -3.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8907 -1.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4399 -2.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7078 -2.8486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8418 -1.3486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3030 -1.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3059 -4.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 20 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 19 26 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 31 2 0 0 0 0 22 18 1 1 0 0 0 22 34 1 0 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 6 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 32 2 0 0 0 0 26 30 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.29
Volume:	509.916
LogP:	5.136
LogD:	4.041
LogS:	-5.463
# Rotatable Bonds:	3
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	5.119
Fsp3:	0.633
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.914
MDCK Permeability:	2.4276587282656692e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.146
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	94.49100494384766%
Volume Distribution (VD):	1.466
Pgp-substrate:	7.493913173675537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.781
CYP2C19-inhibitor:	0.799
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.707
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	6.354
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.516
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.274
Carcinogencity:	0.404
Eye Corrosion:	0.005
Eye Irritation:	0.014
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC474844

Natural Product ID:	NPC474844
*Common Name:**	22,23-Dihydrostellettin B
IUPAC Name:	(3Z,3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-3-[(3E,5E)-6-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]hepta-3,5-dien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione
Synonyms:
Standard InCHIKey:	SZTYRCIANMNHDG-RUJZWOBDSA-N
Standard InCHI:	InChI=1S/C30H40O4/c1-18(22-12-11-20(3)27(33)34-22)9-8-10-19(2)26-21(31)17-24-29(6)16-14-25(32)28(4,5)23(29)13-15-30(24,26)7/h8-11,22-24H,12-17H2,1-7H3/b10-8+,18-9+,26-19+/t22-,23-,24-,29-,30-/m0/s1
SMILES:	C/C(=CC=CC(=C1/C(=O)C[C@@H]2[C@]1(C)CC[C@@H]1[C@]2(C)CCC(=O)C1(C)C)C)/[C@@H]1CC=C(C(=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484851
PubChem CID:	21574218
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620246]
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18826276]

☑ 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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[533356]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[533356]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[533356]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[533356]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[533356]

☑ 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 NPC474844 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	197
0.1-0.2	1125
0.2-0.3	4794
0.3-0.4	12899
0.4-0.5	10190
0.5-0.6	8173
0.6-0.7	4454
0.7-0.8	803
0.8-0.85	52
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC163016
0.9294	High Similarity	NPC75315
0.9277	High Similarity	NPC474790
0.9277	High Similarity	NPC474976
0.8929	High Similarity	NPC94200
0.8824	High Similarity	NPC118423
0.8791	High Similarity	NPC33473
0.8736	High Similarity	NPC168248
0.8723	High Similarity	NPC194028
0.8723	High Similarity	NPC168319
0.8706	High Similarity	NPC268122
0.8602	High Similarity	NPC110937
0.8526	High Similarity	NPC310981
0.8511	High Similarity	NPC98868
0.8488	Intermediate Similarity	NPC469805
0.8488	Intermediate Similarity	NPC469804
0.8444	Intermediate Similarity	NPC177141
0.8404	Intermediate Similarity	NPC2049
0.8391	Intermediate Similarity	NPC3856
0.8391	Intermediate Similarity	NPC279639
0.8367	Intermediate Similarity	NPC266570
0.8353	Intermediate Similarity	NPC190211
0.8352	Intermediate Similarity	NPC474842
0.8352	Intermediate Similarity	NPC475965
0.8352	Intermediate Similarity	NPC220454
0.8352	Intermediate Similarity	NPC469595
0.8352	Intermediate Similarity	NPC273199
0.8352	Intermediate Similarity	NPC212679
0.8333	Intermediate Similarity	NPC196407
0.8316	Intermediate Similarity	NPC108368
0.8316	Intermediate Similarity	NPC57079
0.8276	Intermediate Similarity	NPC469806
0.8276	Intermediate Similarity	NPC469799
0.8256	Intermediate Similarity	NPC469797
0.8256	Intermediate Similarity	NPC469798
0.8247	Intermediate Similarity	NPC155332
0.8247	Intermediate Similarity	NPC114540
0.8247	Intermediate Similarity	NPC32577
0.8242	Intermediate Similarity	NPC284561
0.8235	Intermediate Similarity	NPC105197
0.8214	Intermediate Similarity	NPC4509
0.8211	Intermediate Similarity	NPC202705
0.82	Intermediate Similarity	NPC220155
0.8193	Intermediate Similarity	NPC20025
0.8193	Intermediate Similarity	NPC474796
0.8193	Intermediate Similarity	NPC329866
0.8193	Intermediate Similarity	NPC474797
0.8191	Intermediate Similarity	NPC281134
0.8182	Intermediate Similarity	NPC189863
0.8172	Intermediate Similarity	NPC469939
0.8152	Intermediate Similarity	NPC469372
0.8137	Intermediate Similarity	NPC474315
0.8111	Intermediate Similarity	NPC472863
0.8111	Intermediate Similarity	NPC220478
0.8095	Intermediate Similarity	NPC65650
0.8085	Intermediate Similarity	NPC477129
0.8085	Intermediate Similarity	NPC477130
0.8065	Intermediate Similarity	NPC473986
0.8065	Intermediate Similarity	NPC474018
0.8041	Intermediate Similarity	NPC266955
0.8023	Intermediate Similarity	NPC470052
0.8022	Intermediate Similarity	NPC477228
0.8022	Intermediate Similarity	NPC476293
0.8	Intermediate Similarity	NPC469796
0.8	Intermediate Similarity	NPC209355
0.8	Intermediate Similarity	NPC474463
0.8	Intermediate Similarity	NPC171395
0.8	Intermediate Similarity	NPC469793
0.8	Intermediate Similarity	NPC189311
0.798	Intermediate Similarity	NPC475526
0.798	Intermediate Similarity	NPC329345
0.798	Intermediate Similarity	NPC473283
0.7979	Intermediate Similarity	NPC242069
0.7979	Intermediate Similarity	NPC229976
0.7959	Intermediate Similarity	NPC115899
0.7959	Intermediate Similarity	NPC99411
0.7938	Intermediate Similarity	NPC252295
0.7935	Intermediate Similarity	NPC97884
0.7935	Intermediate Similarity	NPC472302
0.7935	Intermediate Similarity	NPC472220
0.7921	Intermediate Similarity	NPC91034
0.7921	Intermediate Similarity	NPC475294
0.7917	Intermediate Similarity	NPC301534
0.7917	Intermediate Similarity	NPC106425
0.7917	Intermediate Similarity	NPC250757
0.7917	Intermediate Similarity	NPC151725
0.7917	Intermediate Similarity	NPC112654
0.7917	Intermediate Similarity	NPC122324
0.7912	Intermediate Similarity	NPC195640
0.7907	Intermediate Similarity	NPC470557
0.79	Intermediate Similarity	NPC189616
0.7895	Intermediate Similarity	NPC473280
0.7895	Intermediate Similarity	NPC120351
0.7895	Intermediate Similarity	NPC473435
0.7895	Intermediate Similarity	NPC471994
0.7895	Intermediate Similarity	NPC471078
0.7895	Intermediate Similarity	NPC166143
0.7895	Intermediate Similarity	NPC38830
0.7895	Intermediate Similarity	NPC473431
0.7889	Intermediate Similarity	NPC87552
0.7879	Intermediate Similarity	NPC320447
0.7872	Intermediate Similarity	NPC190442
0.7872	Intermediate Similarity	NPC218301
0.7865	Intermediate Similarity	NPC200513
0.7865	Intermediate Similarity	NPC472239
0.7864	Intermediate Similarity	NPC16270
0.7857	Intermediate Similarity	NPC276336
0.7849	Intermediate Similarity	NPC285982
0.7843	Intermediate Similarity	NPC473482
0.7843	Intermediate Similarity	NPC318363
0.7843	Intermediate Similarity	NPC475418
0.7835	Intermediate Similarity	NPC38530
0.7835	Intermediate Similarity	NPC84335
0.7835	Intermediate Similarity	NPC253826
0.7812	Intermediate Similarity	NPC295347
0.7812	Intermediate Similarity	NPC293052
0.7802	Intermediate Similarity	NPC323765
0.7802	Intermediate Similarity	NPC470048
0.7802	Intermediate Similarity	NPC60350
0.78	Intermediate Similarity	NPC72151
0.7789	Intermediate Similarity	NPC79117
0.7778	Intermediate Similarity	NPC470047
0.7778	Intermediate Similarity	NPC470046
0.7778	Intermediate Similarity	NPC193198
0.7767	Intermediate Similarity	NPC475065
0.7767	Intermediate Similarity	NPC228477
0.7767	Intermediate Similarity	NPC137911
0.7766	Intermediate Similarity	NPC8062
0.7766	Intermediate Similarity	NPC161638
0.7755	Intermediate Similarity	NPC176845
0.7755	Intermediate Similarity	NPC235464
0.7755	Intermediate Similarity	NPC166745
0.7745	Intermediate Similarity	NPC330011
0.7745	Intermediate Similarity	NPC476958
0.7745	Intermediate Similarity	NPC329048
0.7742	Intermediate Similarity	NPC226863
0.7742	Intermediate Similarity	NPC215831
0.7742	Intermediate Similarity	NPC473879
0.7738	Intermediate Similarity	NPC54123
0.7732	Intermediate Similarity	NPC307164
0.7732	Intermediate Similarity	NPC111684
0.7732	Intermediate Similarity	NPC58052
0.7727	Intermediate Similarity	NPC170793
0.7727	Intermediate Similarity	NPC471299
0.7723	Intermediate Similarity	NPC472868
0.7717	Intermediate Similarity	NPC470050
0.7717	Intermediate Similarity	NPC264127
0.7717	Intermediate Similarity	NPC470051
0.7708	Intermediate Similarity	NPC84893
0.77	Intermediate Similarity	NPC475320
0.7692	Intermediate Similarity	NPC473627
0.7692	Intermediate Similarity	NPC181743
0.7692	Intermediate Similarity	NPC178025
0.7692	Intermediate Similarity	NPC16287
0.7692	Intermediate Similarity	NPC475100
0.7692	Intermediate Similarity	NPC37116
0.7692	Intermediate Similarity	NPC149869
0.7684	Intermediate Similarity	NPC23217
0.7684	Intermediate Similarity	NPC303697
0.7677	Intermediate Similarity	NPC470906
0.7677	Intermediate Similarity	NPC201406
0.7677	Intermediate Similarity	NPC35751
0.7677	Intermediate Similarity	NPC477720
0.7674	Intermediate Similarity	NPC473171
0.7667	Intermediate Similarity	NPC327969
0.7667	Intermediate Similarity	NPC16321
0.7667	Intermediate Similarity	NPC142253
0.7667	Intermediate Similarity	NPC321289
0.7667	Intermediate Similarity	NPC100297
0.7667	Intermediate Similarity	NPC472867
0.7667	Intermediate Similarity	NPC3511
0.766	Intermediate Similarity	NPC174342
0.766	Intermediate Similarity	NPC73995
0.766	Intermediate Similarity	NPC5509
0.766	Intermediate Similarity	NPC471654
0.7653	Intermediate Similarity	NPC208094
0.7653	Intermediate Similarity	NPC151488
0.7647	Intermediate Similarity	NPC127790
0.7647	Intermediate Similarity	NPC251705
0.7647	Intermediate Similarity	NPC474228
0.7647	Intermediate Similarity	NPC303613
0.7642	Intermediate Similarity	NPC122056
0.764	Intermediate Similarity	NPC474509
0.7629	Intermediate Similarity	NPC476174
0.7624	Intermediate Similarity	NPC112009
0.7624	Intermediate Similarity	NPC180204
0.7624	Intermediate Similarity	NPC470954
0.7619	Intermediate Similarity	NPC265782
0.7619	Intermediate Similarity	NPC2634
0.7619	Intermediate Similarity	NPC251929
0.7609	Intermediate Similarity	NPC137493
0.7609	Intermediate Similarity	NPC8571
0.7609	Intermediate Similarity	NPC65661
0.7604	Intermediate Similarity	NPC475657
0.7604	Intermediate Similarity	NPC474185
0.76	Intermediate Similarity	NPC282524
0.7586	Intermediate Similarity	NPC69408
0.7586	Intermediate Similarity	NPC27205
0.7582	Intermediate Similarity	NPC22611
0.7582	Intermediate Similarity	NPC16488

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 NPC474844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1145
0.2-0.3	3879
0.3-0.4	2714
0.4-0.5	778
0.5-0.6	235
0.6-0.7	186
0.7-0.8	51
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7976	Intermediate Similarity	NPD4058	Approved
0.7912	Intermediate Similarity	NPD6409	Approved
0.7912	Intermediate Similarity	NPD7334	Approved
0.7912	Intermediate Similarity	NPD5330	Approved
0.7912	Intermediate Similarity	NPD7146	Approved
0.7912	Intermediate Similarity	NPD6684	Approved
0.7912	Intermediate Similarity	NPD7521	Approved
0.7865	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6672	Approved
0.7742	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD5737	Approved
0.7742	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4691	Approved
0.7558	Intermediate Similarity	NPD4687	Approved
0.7558	Intermediate Similarity	NPD5733	Approved
0.75	Intermediate Similarity	NPD4137	Phase 3
0.75	Intermediate Similarity	NPD5693	Phase 1
0.7431	Intermediate Similarity	NPD7115	Discovery
0.7423	Intermediate Similarity	NPD6399	Phase 3
0.7419	Intermediate Similarity	NPD1694	Approved
0.7412	Intermediate Similarity	NPD4747	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.7326	Intermediate Similarity	NPD5276	Approved
0.732	Intermediate Similarity	NPD6050	Approved
0.732	Intermediate Similarity	NPD5694	Approved
0.7292	Intermediate Similarity	NPD6904	Approved
0.7292	Intermediate Similarity	NPD6673	Approved
0.7292	Intermediate Similarity	NPD6080	Approved
0.7283	Intermediate Similarity	NPD5209	Approved
0.7216	Intermediate Similarity	NPD5207	Approved
0.7216	Intermediate Similarity	NPD5692	Phase 3
0.7216	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD6051	Approved
0.71	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8039	Approved
0.7021	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5208	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD6098	Approved
0.6977	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6079	Approved
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6947	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD3668	Phase 3
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6947	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD5695	Phase 3
0.6916	Remote Similarity	NPD5697	Approved
0.6915	Remote Similarity	NPD3667	Approved
0.6907	Remote Similarity	NPD3573	Approved
0.6905	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5696	Approved
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6852	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6804	Remote Similarity	NPD5279	Phase 3
0.6804	Remote Similarity	NPD3618	Phase 1
0.68	Remote Similarity	NPD7515	Phase 2
0.6796	Remote Similarity	NPD7902	Approved
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD6014	Approved
0.6768	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5328	Approved
0.6765	Remote Similarity	NPD5654	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6701	Remote Similarity	NPD5363	Approved
0.6699	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5222	Approved
0.6699	Remote Similarity	NPD5221	Approved
0.6698	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD7094	Approved
0.6696	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6635	Remote Similarity	NPD5173	Approved
0.6635	Remote Similarity	NPD5959	Approved
0.6634	Remote Similarity	NPD6411	Approved
0.6607	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD6614	Approved
0.6602	Remote Similarity	NPD5210	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD4753	Phase 2
0.6598	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6868	Approved
0.6562	Remote Similarity	NPD4223	Phase 3
0.6562	Remote Similarity	NPD4221	Approved
0.6542	Remote Similarity	NPD5211	Phase 2
0.6531	Remote Similarity	NPD5329	Approved
0.6526	Remote Similarity	NPD4695	Discontinued
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD4696	Approved
0.6509	Remote Similarity	NPD6404	Discontinued
0.6509	Remote Similarity	NPD5285	Approved
0.6504	Remote Similarity	NPD7260	Phase 2
0.6495	Remote Similarity	NPD5362	Discontinued
0.6481	Remote Similarity	NPD6052	Approved
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD6335	Approved
0.6465	Remote Similarity	NPD5280	Approved
0.6465	Remote Similarity	NPD4694	Approved
0.6465	Remote Similarity	NPD5690	Phase 2
0.6465	Remote Similarity	NPD4623	Approved
0.6465	Remote Similarity	NPD4519	Discontinued
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6412	Phase 2
0.6449	Remote Similarity	NPD5223	Approved
0.6442	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7503	Approved
0.6436	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6101	Approved
0.6429	Remote Similarity	NPD4197	Approved
0.6422	Remote Similarity	NPD5141	Approved
0.641	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD7101	Approved
0.6408	Remote Similarity	NPD4202	Approved
0.6408	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5779	Approved
0.6404	Remote Similarity	NPD4632	Approved
0.6392	Remote Similarity	NPD4269	Approved
0.6392	Remote Similarity	NPD4270	Approved
0.6389	Remote Similarity	NPD5226	Approved
0.6389	Remote Similarity	NPD4633	Approved
0.6389	Remote Similarity	NPD5225	Approved
0.6389	Remote Similarity	NPD5224	Approved
0.6381	Remote Similarity	NPD7732	Phase 3
0.6381	Remote Similarity	NPD4697	Phase 3
0.6379	Remote Similarity	NPD6317	Approved
0.6374	Remote Similarity	NPD5777	Approved
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4252	Approved
0.6354	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5174	Approved
0.633	Remote Similarity	NPD5175	Approved
0.6327	Remote Similarity	NPD7154	Phase 3
0.6327	Remote Similarity	NPD4788	Approved
0.6325	Remote Similarity	NPD6313	Approved
0.6325	Remote Similarity	NPD6314	Approved
0.6321	Remote Similarity	NPD4755	Approved
0.6316	Remote Similarity	NPD3617	Approved
0.6306	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4689	Approved
0.63	Remote Similarity	NPD4688	Approved
0.63	Remote Similarity	NPD4693	Phase 3
0.63	Remote Similarity	NPD5205	Approved
0.63	Remote Similarity	NPD4138	Approved
0.63	Remote Similarity	NPD4690	Approved
0.63	Remote Similarity	NPD5786	Approved
0.6293	Remote Similarity	NPD6274	Approved
0.6289	Remote Similarity	NPD8028	Phase 2
0.6289	Remote Similarity	NPD5369	Approved
0.6264	Remote Similarity	NPD7144	Approved
0.6264	Remote Similarity	NPD7143	Approved
0.625	Remote Similarity	NPD4195	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.623	Remote Similarity	NPD7507	Approved
0.6224	Remote Similarity	NPD6435	Approved
0.6218	Remote Similarity	NPD6319	Approved
0.6214	Remote Similarity	NPD6698	Approved
0.6214	Remote Similarity	NPD46	Approved
0.6204	Remote Similarity	NPD4700	Approved
0.6198	Remote Similarity	NPD7604	Phase 2
0.6196	Remote Similarity	NPD7150	Approved
0.6196	Remote Similarity	NPD7151	Approved
0.6196	Remote Similarity	NPD7152	Approved
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5790	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