NPASS Compound

Structure

NPC473258 OpenBabel07101719522D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.8047 -1.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8159 -1.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 1.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5812 -0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9223 -4.5778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6490 -3.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 -4.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2603 -4.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7471 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8811 -2.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1674 -2.0852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2407 -0.1679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 -1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0101 -2.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6075 -4.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5384 -3.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 -2.9888 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.3950 -2.7203 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.7603 -3.6511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0151 -2.4888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6774 0.6583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1490 -0.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4394 -2.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0151 -1.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7585 -3.5913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1490 -2.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4585 -5.3402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1774 1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6947 -3.9427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 -3.8549 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 28 1 6 0 0 0 25 35 1 0 0 0 0 27 35 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 33 1 0 0 0 0 30 7 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.38
Volume:	534.525
LogP:	4.547
LogD:	3.924
LogS:	-4.715
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	5.301
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.735
MDCK Permeability:	2.342116022191476e-05
Pgp-inhibitor:	0.888
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.834
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	93.49987030029297%
Volume Distribution (VD):	1.09
Pgp-substrate:	4.180410385131836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.371
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.284
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	5.098
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.239
Carcinogencity:	0.014
Eye Corrosion:	0.004
Eye Irritation:	0.058
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC473258

Natural Product ID:	NPC473258
*Common Name:**	28-Hydroxysipholenol A
IUPAC Name:	(3R,5aR,6R,7S,9aR)-6-[2-[(1R)-1-hydroxy-6-(hydroxymethyl)-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
Synonyms:
Standard InCHIKey:	WWNUXCFWCRMYCN-NXHAIPTASA-N
Standard InCHI:	InChI=1S/C30H52O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,20-25,31-34H,9-18H2,1-7H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1
SMILES:	OCC1=CCC2C(C(C1CC[C@H]1[C@@](C)(O)CC[C@@H]3[C@]1(C)CC[C@H](C(O3)(C)C)O)(C)C)CC[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388091
PubChem CID:	16738312
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
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	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	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	5.9	nM	PMID[480429]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[480429]
NPT2	Others	Unspecified		IC50	=	5070.0	nM	PMID[480429]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[480429]

☑ 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 NPC473258 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	191
0.1-0.2	1697
0.2-0.3	5626
0.3-0.4	14807
0.4-0.5	8710
0.5-0.6	7290
0.6-0.7	3931
0.7-0.8	411
0.8-0.85	31
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC470832
0.8681	High Similarity	NPC115607
0.8495	Intermediate Similarity	NPC210268
0.8485	Intermediate Similarity	NPC470838
0.8478	Intermediate Similarity	NPC97103
0.8444	Intermediate Similarity	NPC290731
0.8384	Intermediate Similarity	NPC473694
0.8384	Intermediate Similarity	NPC475623
0.8384	Intermediate Similarity	NPC475334
0.8352	Intermediate Similarity	NPC476217
0.83	Intermediate Similarity	NPC181104
0.83	Intermediate Similarity	NPC475331
0.83	Intermediate Similarity	NPC475335
0.83	Intermediate Similarity	NPC80809
0.83	Intermediate Similarity	NPC201144
0.83	Intermediate Similarity	NPC121518
0.83	Intermediate Similarity	NPC103298
0.83	Intermediate Similarity	NPC288502
0.8298	Intermediate Similarity	NPC94127
0.8261	Intermediate Similarity	NPC189777
0.8218	Intermediate Similarity	NPC60315
0.8119	Intermediate Similarity	NPC473577
0.8119	Intermediate Similarity	NPC475585
0.8119	Intermediate Similarity	NPC474550
0.81	Intermediate Similarity	NPC470840
0.8065	Intermediate Similarity	NPC233744
0.8061	Intermediate Similarity	NPC261807
0.8039	Intermediate Similarity	NPC475290
0.8021	Intermediate Similarity	NPC98193
0.798	Intermediate Similarity	NPC476895
0.7979	Intermediate Similarity	NPC133588
0.7979	Intermediate Similarity	NPC474668
0.7959	Intermediate Similarity	NPC288970
0.7959	Intermediate Similarity	NPC103165
0.7959	Intermediate Similarity	NPC72204
0.7959	Intermediate Similarity	NPC210717
0.7957	Intermediate Similarity	NPC139724
0.7917	Intermediate Similarity	NPC41554
0.7917	Intermediate Similarity	NPC97404
0.7895	Intermediate Similarity	NPC470361
0.7879	Intermediate Similarity	NPC475033
0.7879	Intermediate Similarity	NPC475032
0.7879	Intermediate Similarity	NPC476893
0.7872	Intermediate Similarity	NPC476948
0.7857	Intermediate Similarity	NPC86893
0.7857	Intermediate Similarity	NPC292178
0.7857	Intermediate Similarity	NPC8774
0.7857	Intermediate Similarity	NPC476894
0.7841	Intermediate Similarity	NPC126969
0.7835	Intermediate Similarity	NPC137461
0.7826	Intermediate Similarity	NPC110778
0.7822	Intermediate Similarity	NPC476896
0.7812	Intermediate Similarity	NPC3345
0.7812	Intermediate Similarity	NPC295668
0.7812	Intermediate Similarity	NPC291484
0.7812	Intermediate Similarity	NPC80561
0.7812	Intermediate Similarity	NPC11216
0.7812	Intermediate Similarity	NPC329596
0.7812	Intermediate Similarity	NPC204188
0.7802	Intermediate Similarity	NPC473257
0.7789	Intermediate Similarity	NPC471952
0.7789	Intermediate Similarity	NPC22376
0.7789	Intermediate Similarity	NPC280556
0.7778	Intermediate Similarity	NPC12103
0.7778	Intermediate Similarity	NPC227583
0.7778	Intermediate Similarity	NPC98457
0.7766	Intermediate Similarity	NPC261266
0.7766	Intermediate Similarity	NPC293287
0.7766	Intermediate Similarity	NPC152808
0.7766	Intermediate Similarity	NPC6391
0.7766	Intermediate Similarity	NPC201273
0.7755	Intermediate Similarity	NPC65402
0.7755	Intermediate Similarity	NPC127718
0.7745	Intermediate Similarity	NPC470972
0.7742	Intermediate Similarity	NPC15534
0.7742	Intermediate Similarity	NPC124172
0.7732	Intermediate Similarity	NPC114389
0.7723	Intermediate Similarity	NPC475877
0.7723	Intermediate Similarity	NPC471242
0.7708	Intermediate Similarity	NPC105495
0.7708	Intermediate Similarity	NPC109744
0.77	Intermediate Similarity	NPC254121
0.77	Intermediate Similarity	NPC26307
0.77	Intermediate Similarity	NPC476021
0.77	Intermediate Similarity	NPC476040
0.77	Intermediate Similarity	NPC474994
0.77	Intermediate Similarity	NPC470834
0.77	Intermediate Similarity	NPC477226
0.7692	Intermediate Similarity	NPC472899
0.7692	Intermediate Similarity	NPC472898
0.7692	Intermediate Similarity	NPC471266
0.7692	Intermediate Similarity	NPC95124
0.7692	Intermediate Similarity	NPC472900
0.7684	Intermediate Similarity	NPC186145
0.7684	Intermediate Similarity	NPC474657
0.7677	Intermediate Similarity	NPC476720
0.767	Intermediate Similarity	NPC475701
0.767	Intermediate Similarity	NPC472821
0.767	Intermediate Similarity	NPC473523
0.767	Intermediate Similarity	NPC160583
0.766	Intermediate Similarity	NPC318390
0.7653	Intermediate Similarity	NPC310013
0.7653	Intermediate Similarity	NPC119379
0.7647	Intermediate Similarity	NPC155974
0.7647	Intermediate Similarity	NPC475617
0.7634	Intermediate Similarity	NPC207013
0.7634	Intermediate Similarity	NPC477818
0.7634	Intermediate Similarity	NPC193870
0.7634	Intermediate Similarity	NPC471340
0.7634	Intermediate Similarity	NPC474634
0.7634	Intermediate Similarity	NPC141941
0.7629	Intermediate Similarity	NPC475751
0.7629	Intermediate Similarity	NPC473956
0.7624	Intermediate Similarity	NPC5358
0.7624	Intermediate Similarity	NPC470067
0.7624	Intermediate Similarity	NPC470066
0.7624	Intermediate Similarity	NPC216260
0.7619	Intermediate Similarity	NPC231340
0.7615	Intermediate Similarity	NPC216665
0.7609	Intermediate Similarity	NPC471270
0.7609	Intermediate Similarity	NPC70927
0.7604	Intermediate Similarity	NPC67872
0.7604	Intermediate Similarity	NPC475664
0.76	Intermediate Similarity	NPC90583
0.7596	Intermediate Similarity	NPC152966
0.7596	Intermediate Similarity	NPC473543
0.7596	Intermediate Similarity	NPC474464
0.7596	Intermediate Similarity	NPC75608
0.7593	Intermediate Similarity	NPC477050
0.7593	Intermediate Similarity	NPC216595
0.7593	Intermediate Similarity	NPC473567
0.7579	Intermediate Similarity	NPC24277
0.7579	Intermediate Similarity	NPC6605
0.7579	Intermediate Similarity	NPC125399
0.7579	Intermediate Similarity	NPC299068
0.7576	Intermediate Similarity	NPC144202
0.7576	Intermediate Similarity	NPC474922
0.7573	Intermediate Similarity	NPC165578
0.7573	Intermediate Similarity	NPC22634
0.7553	Intermediate Similarity	NPC475798
0.7553	Intermediate Similarity	NPC102048
0.7553	Intermediate Similarity	NPC185568
0.7553	Intermediate Similarity	NPC83702
0.7553	Intermediate Similarity	NPC474047
0.7553	Intermediate Similarity	NPC242016
0.7553	Intermediate Similarity	NPC127606
0.7551	Intermediate Similarity	NPC249034
0.7551	Intermediate Similarity	NPC275671
0.7551	Intermediate Similarity	NPC472468
0.7549	Intermediate Similarity	NPC208358
0.7527	Intermediate Similarity	NPC470614
0.7527	Intermediate Similarity	NPC87489
0.7527	Intermediate Similarity	NPC472465
0.7527	Intermediate Similarity	NPC218616
0.7527	Intermediate Similarity	NPC1272
0.7527	Intermediate Similarity	NPC30166
0.7527	Intermediate Similarity	NPC296701
0.7526	Intermediate Similarity	NPC477917
0.7525	Intermediate Similarity	NPC316604
0.7525	Intermediate Similarity	NPC272451
0.7525	Intermediate Similarity	NPC210337
0.7524	Intermediate Similarity	NPC186668
0.7524	Intermediate Similarity	NPC474015
0.7524	Intermediate Similarity	NPC470980
0.7523	Intermediate Similarity	NPC317210
0.75	Intermediate Similarity	NPC13554
0.75	Intermediate Similarity	NPC473198
0.75	Intermediate Similarity	NPC236237
0.75	Intermediate Similarity	NPC322313
0.75	Intermediate Similarity	NPC236707
0.75	Intermediate Similarity	NPC102253
0.75	Intermediate Similarity	NPC474124
0.75	Intermediate Similarity	NPC470620
0.7477	Intermediate Similarity	NPC128133
0.7476	Intermediate Similarity	NPC88000
0.7476	Intermediate Similarity	NPC309425
0.7476	Intermediate Similarity	NPC160734
0.7476	Intermediate Similarity	NPC222875
0.7476	Intermediate Similarity	NPC472023
0.7476	Intermediate Similarity	NPC268829
0.7476	Intermediate Similarity	NPC247701
0.7476	Intermediate Similarity	NPC4831
0.7476	Intermediate Similarity	NPC295110
0.7476	Intermediate Similarity	NPC25177
0.7476	Intermediate Similarity	NPC129372
0.7476	Intermediate Similarity	NPC47566
0.7476	Intermediate Similarity	NPC470434
0.7475	Intermediate Similarity	NPC27531
0.7475	Intermediate Similarity	NPC296620
0.7474	Intermediate Similarity	NPC470360
0.7455	Intermediate Similarity	NPC326542
0.7455	Intermediate Similarity	NPC43213
0.7453	Intermediate Similarity	NPC476594
0.7451	Intermediate Similarity	NPC309493
0.7451	Intermediate Similarity	NPC234287
0.7451	Intermediate Similarity	NPC275865
0.7451	Intermediate Similarity	NPC280825
0.7449	Intermediate Similarity	NPC472466
0.7449	Intermediate Similarity	NPC191323
0.7449	Intermediate Similarity	NPC209816

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 NPC473258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2095
0.2-0.3	4214
0.3-0.4	1889
0.4-0.5	407
0.5-0.6	226
0.6-0.7	136
0.7-0.8	5
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
0.7684	Intermediate Similarity	NPD7524	Approved
0.7553	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7525	Registered
0.7447	Intermediate Similarity	NPD6695	Phase 3
0.732	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7327	Approved
0.7257	Intermediate Similarity	NPD7328	Approved
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.7193	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7128	Intermediate Similarity	NPD6931	Approved
0.7128	Intermediate Similarity	NPD6930	Phase 2
0.7115	Intermediate Similarity	NPD7638	Approved
0.7065	Intermediate Similarity	NPD6933	Approved
0.7021	Intermediate Similarity	NPD6929	Approved
0.6983	Remote Similarity	NPD8377	Approved
0.6983	Remote Similarity	NPD8294	Approved
0.6981	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD7514	Phase 3
0.6923	Remote Similarity	NPD8296	Approved
0.6923	Remote Similarity	NPD8378	Approved
0.6923	Remote Similarity	NPD8033	Approved
0.6923	Remote Similarity	NPD8335	Approved
0.6923	Remote Similarity	NPD8380	Approved
0.6923	Remote Similarity	NPD8379	Approved
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7087	Discontinued
0.6848	Remote Similarity	NPD6926	Approved
0.6848	Remote Similarity	NPD6924	Approved
0.6809	Remote Similarity	NPD6925	Approved
0.6809	Remote Similarity	NPD5776	Phase 2
0.6786	Remote Similarity	NPD6371	Approved
0.678	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD7339	Approved
0.6771	Remote Similarity	NPD7332	Phase 2
0.6768	Remote Similarity	NPD6893	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6737	Remote Similarity	NPD7145	Approved
0.6701	Remote Similarity	NPD6902	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD4202	Approved
0.6632	Remote Similarity	NPD6932	Approved
0.663	Remote Similarity	NPD4243	Approved
0.6606	Remote Similarity	NPD5211	Phase 2
0.6606	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD4748	Discontinued
0.6598	Remote Similarity	NPD7509	Discontinued
0.6577	Remote Similarity	NPD5739	Approved
0.6577	Remote Similarity	NPD7128	Approved
0.6577	Remote Similarity	NPD6675	Approved
0.6577	Remote Similarity	NPD6402	Approved
0.6574	Remote Similarity	NPD6648	Approved
0.6562	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6054	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6555	Remote Similarity	NPD6059	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6538	Remote Similarity	NPD7637	Suspended
0.6532	Remote Similarity	NPD7319	Approved
0.6531	Remote Similarity	NPD6898	Phase 1
0.6522	Remote Similarity	NPD8297	Approved
0.6514	Remote Similarity	NPD4159	Approved
0.6505	Remote Similarity	NPD6051	Approved
0.6495	Remote Similarity	NPD6683	Phase 2
0.6495	Remote Similarity	NPD7645	Phase 2
0.6491	Remote Similarity	NPD4634	Approved
0.6489	Remote Similarity	NPD4784	Approved
0.6489	Remote Similarity	NPD4785	Approved
0.6486	Remote Similarity	NPD5141	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD7320	Approved
0.646	Remote Similarity	NPD6899	Approved
0.6452	Remote Similarity	NPD7150	Approved
0.6452	Remote Similarity	NPD7151	Approved
0.6452	Remote Similarity	NPD7152	Approved
0.6446	Remote Similarity	NPD6370	Approved
0.6442	Remote Similarity	NPD3168	Discontinued
0.6441	Remote Similarity	NPD6009	Approved
0.6441	Remote Similarity	NPD7115	Discovery
0.6422	Remote Similarity	NPD5286	Approved
0.6422	Remote Similarity	NPD5285	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6422	Remote Similarity	NPD4696	Approved
0.6421	Remote Similarity	NPD8264	Approved
0.6413	Remote Similarity	NPD6923	Approved
0.6413	Remote Similarity	NPD6922	Approved
0.6404	Remote Similarity	NPD6373	Approved
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6372	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6379	Remote Similarity	NPD6053	Discontinued
0.6372	Remote Similarity	NPD5697	Approved
0.6372	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6348	Remote Similarity	NPD7290	Approved
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.6346	Remote Similarity	NPD5328	Approved
0.6344	Remote Similarity	NPD7144	Approved
0.6344	Remote Similarity	NPD7143	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6337	Remote Similarity	NPD4786	Approved
0.6321	Remote Similarity	NPD6399	Phase 3
0.6316	Remote Similarity	NPD6686	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6311	Remote Similarity	NPD5988	Approved
0.6311	Remote Similarity	NPD4250	Approved
0.6311	Remote Similarity	NPD4251	Approved
0.6306	Remote Similarity	NPD5225	Approved
0.6306	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD5226	Approved
0.6306	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD6649	Approved
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6650	Approved
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD8130	Phase 1
0.6293	Remote Similarity	NPD6869	Approved
0.629	Remote Similarity	NPD6336	Discontinued
0.629	Remote Similarity	NPD6616	Approved
0.6283	Remote Similarity	NPD6640	Phase 3
0.6283	Remote Similarity	NPD6008	Approved
0.6275	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4821	Approved
0.6263	Remote Similarity	NPD4819	Approved
0.6263	Remote Similarity	NPD4822	Approved
0.6263	Remote Similarity	NPD4820	Approved
0.6263	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6013	Approved
0.6261	Remote Similarity	NPD6012	Approved
0.6261	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD4190	Phase 3
0.625	Remote Similarity	NPD5275	Approved
0.625	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD5174	Approved
0.624	Remote Similarity	NPD7078	Approved
0.624	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD6083	Phase 2
0.6238	Remote Similarity	NPD5362	Discontinued
0.6237	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6079	Approved
0.6214	Remote Similarity	NPD3618	Phase 1
0.6214	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD4753	Phase 2
0.619	Remote Similarity	NPD7736	Approved
0.619	Remote Similarity	NPD6033	Approved
0.6186	Remote Similarity	NPD8133	Approved
0.618	Remote Similarity	NPD368	Approved
0.6176	Remote Similarity	NPD3133	Approved
0.6176	Remote Similarity	NPD3666	Approved
0.6176	Remote Similarity	NPD3665	Phase 1
0.6162	Remote Similarity	NPD4195	Approved
0.6147	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4767	Approved
0.614	Remote Similarity	NPD4768	Approved
0.6139	Remote Similarity	NPD3667	Approved
0.6129	Remote Similarity	NPD6067	Discontinued
0.61	Remote Similarity	NPD6928	Phase 2
0.6087	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD5332	Approved
0.6075	Remote Similarity	NPD8034	Phase 2
0.6075	Remote Similarity	NPD8035	Phase 2
0.6068	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4271	Approved
0.6061	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4268	Approved
0.6055	Remote Similarity	NPD5695	Phase 3
0.604	Remote Similarity	NPD4790	Discontinued
0.6034	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4729	Approved
0.6034	Remote Similarity	NPD5128	Approved
0.6034	Remote Similarity	NPD4730	Approved
0.6019	Remote Similarity	NPD8171	Discontinued
0.6	Remote Similarity	NPD5357	Phase 1
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5984	Remote Similarity	NPD6335	Approved
0.5981	Remote Similarity	NPD46	Approved
0.5981	Remote Similarity	NPD7838	Discovery
0.5981	Remote Similarity	NPD7136	Phase 2
0.5981	Remote Similarity	NPD6698	Approved
0.598	Remote Similarity	NPD4221	Approved
0.598	Remote Similarity	NPD4223	Phase 3
0.5962	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5329	Approved
0.595	Remote Similarity	NPD6274	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