NPASS Compound

Structure

NPC109512 OpenBabel07101719142D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.8234 -3.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 -2.1488 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 -3.8745 -1.1977 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 -1.2024 1.0827 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 2.5981 -3.5000 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 -0.2079 0.9781 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 -3.5144 -2.8920 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 -0.9898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -2.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -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 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8671 -3.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 -1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 2 1 1 0 0 0 19 20 1 0 0 0 0 20 29 1 1 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 19 1 1 0 0 0 23 33 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 31 2 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	5.997
LogD:	4.694
LogS:	-6.274
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	4.91
Fsp3:	0.867
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:	-5.042
MDCK Permeability:	1.827043161028996e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	91.75424194335938%
Volume Distribution (VD):	1.221
Pgp-substrate:	1.2212448120117188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.537
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.973
CYP2C9-inhibitor:	0.322
CYP2C9-substrate:	0.736
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.638
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	6.415
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.353
Drug-inuced Liver Injury (DILI):	0.432
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.778
Skin Sensitization:	0.097
Carcinogencity:	0.113
Eye Corrosion:	0.01
Eye Irritation:	0.094
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC109512

Natural Product ID:	NPC109512
*Common Name:**	Astrahygrone
IUPAC Name:	(3S,6S)-3-methyl-6-[(1S)-1-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]oxan-2-one
Synonyms:	Astrahygrone
Standard InCHIKey:	ZDIXYHJVIOUKKS-HEMYKJJBSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-18-8-10-23(33-26(18)32)19(2)20-12-16-30(7)22-9-11-24-27(3,4)25(31)14-15-28(24,5)21(22)13-17-29(20,30)6/h18-20,23-24H,8-17H2,1-7H3/t18-,19-,20+,23-,24-,28+,29+,30-/m0/s1
SMILES:	C[C@H]1CC[C@@H]([C@@H](C)[C@H]2CC[C@@]3(C)C4=C(CC[C@]23C)[C@@]2(C)CCC(=O)C(C)(C)[C@@H]2CC4)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454687
PubChem CID:	44563602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO22791	Astraeus pteridis	Species	Astraeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19067555]
NPO22791	Astraeus pteridis	Species	Astraeaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	64.0	ug.mL-1	PMID[550505]

☑ 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 NPC109512 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	200
0.1-0.2	1588
0.2-0.3	7525
0.3-0.4	14968
0.4-0.5	6373
0.5-0.6	6351
0.6-0.7	4418
0.7-0.8	1207
0.8-0.85	59
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC20388
0.8953	High Similarity	NPC218301
0.8556	High Similarity	NPC58052
0.8556	High Similarity	NPC111684
0.8539	High Similarity	NPC184870
0.8471	Intermediate Similarity	NPC470223
0.8452	Intermediate Similarity	NPC271784
0.8427	Intermediate Similarity	NPC470254
0.8409	Intermediate Similarity	NPC219495
0.8409	Intermediate Similarity	NPC289213
0.8391	Intermediate Similarity	NPC28227
0.8372	Intermediate Similarity	NPC195640
0.8372	Intermediate Similarity	NPC264127
0.8353	Intermediate Similarity	NPC100391
0.8352	Intermediate Similarity	NPC42042
0.8333	Intermediate Similarity	NPC327969
0.8333	Intermediate Similarity	NPC321289
0.8315	Intermediate Similarity	NPC150383
0.8315	Intermediate Similarity	NPC107690
0.8295	Intermediate Similarity	NPC474889
0.8295	Intermediate Similarity	NPC473039
0.8261	Intermediate Similarity	NPC216904
0.8261	Intermediate Similarity	NPC121339
0.8256	Intermediate Similarity	NPC323765
0.8242	Intermediate Similarity	NPC470016
0.8242	Intermediate Similarity	NPC317586
0.8235	Intermediate Similarity	NPC469561
0.8222	Intermediate Similarity	NPC25750
0.8222	Intermediate Similarity	NPC206810
0.8214	Intermediate Similarity	NPC201912
0.8214	Intermediate Similarity	NPC38350
0.8211	Intermediate Similarity	NPC470954
0.8202	Intermediate Similarity	NPC175628
0.8202	Intermediate Similarity	NPC148414
0.8202	Intermediate Similarity	NPC111585
0.8191	Intermediate Similarity	NPC474327
0.8182	Intermediate Similarity	NPC472220
0.8182	Intermediate Similarity	NPC97884
0.8172	Intermediate Similarity	NPC275439
0.8172	Intermediate Similarity	NPC112753
0.8161	Intermediate Similarity	NPC28252
0.8161	Intermediate Similarity	NPC55309
0.8152	Intermediate Similarity	NPC125622
0.8152	Intermediate Similarity	NPC3772
0.8152	Intermediate Similarity	NPC328371
0.814	Intermediate Similarity	NPC320801
0.814	Intermediate Similarity	NPC469407
0.8132	Intermediate Similarity	NPC166906
0.8132	Intermediate Similarity	NPC56525
0.8118	Intermediate Similarity	NPC240302
0.8118	Intermediate Similarity	NPC100297
0.8118	Intermediate Similarity	NPC260956
0.8111	Intermediate Similarity	NPC26888
0.809	Intermediate Similarity	NPC54689
0.809	Intermediate Similarity	NPC474679
0.809	Intermediate Similarity	NPC474570
0.8072	Intermediate Similarity	NPC63020
0.8072	Intermediate Similarity	NPC469996
0.8072	Intermediate Similarity	NPC4827
0.8068	Intermediate Similarity	NPC159046
0.8068	Intermediate Similarity	NPC233836
0.8068	Intermediate Similarity	NPC187376
0.8068	Intermediate Similarity	NPC167877
0.8065	Intermediate Similarity	NPC106557
0.8065	Intermediate Similarity	NPC18319
0.8065	Intermediate Similarity	NPC23680
0.8046	Intermediate Similarity	NPC470048
0.8046	Intermediate Similarity	NPC473038
0.8043	Intermediate Similarity	NPC473648
0.8043	Intermediate Similarity	NPC241156
0.8043	Intermediate Similarity	NPC469599
0.8043	Intermediate Similarity	NPC173875
0.8043	Intermediate Similarity	NPC255809
0.8043	Intermediate Similarity	NPC318282
0.8043	Intermediate Similarity	NPC37646
0.8043	Intermediate Similarity	NPC469995
0.8043	Intermediate Similarity	NPC174948
0.8023	Intermediate Similarity	NPC83569
0.8023	Intermediate Similarity	NPC470047
0.8023	Intermediate Similarity	NPC69279
0.8023	Intermediate Similarity	NPC470046
0.8022	Intermediate Similarity	NPC79117
0.8	Intermediate Similarity	NPC124211
0.8	Intermediate Similarity	NPC471896
0.8	Intermediate Similarity	NPC147066
0.8	Intermediate Similarity	NPC310981
0.8	Intermediate Similarity	NPC474955
0.7979	Intermediate Similarity	NPC271387
0.7979	Intermediate Similarity	NPC153792
0.7978	Intermediate Similarity	NPC474845
0.7978	Intermediate Similarity	NPC242864
0.7978	Intermediate Similarity	NPC131470
0.7978	Intermediate Similarity	NPC143767
0.7976	Intermediate Similarity	NPC471475
0.7976	Intermediate Similarity	NPC44083
0.7976	Intermediate Similarity	NPC153987
0.7976	Intermediate Similarity	NPC477371
0.7957	Intermediate Similarity	NPC95565
0.7957	Intermediate Similarity	NPC305483
0.7957	Intermediate Similarity	NPC40765
0.7957	Intermediate Similarity	NPC96859
0.7957	Intermediate Similarity	NPC328162
0.7957	Intermediate Similarity	NPC243525
0.7957	Intermediate Similarity	NPC7124
0.7955	Intermediate Similarity	NPC155011
0.7955	Intermediate Similarity	NPC470051
0.7955	Intermediate Similarity	NPC471042
0.7955	Intermediate Similarity	NPC470050
0.7935	Intermediate Similarity	NPC471720
0.7931	Intermediate Similarity	NPC473246
0.7931	Intermediate Similarity	NPC120158
0.7931	Intermediate Similarity	NPC312660
0.7931	Intermediate Similarity	NPC475509
0.7931	Intermediate Similarity	NPC165064
0.7931	Intermediate Similarity	NPC475193
0.7917	Intermediate Similarity	NPC56498
0.7917	Intermediate Similarity	NPC53222
0.7912	Intermediate Similarity	NPC297265
0.7912	Intermediate Similarity	NPC154101
0.7895	Intermediate Similarity	NPC88198
0.7895	Intermediate Similarity	NPC205899
0.7889	Intermediate Similarity	NPC102414
0.7889	Intermediate Similarity	NPC86319
0.7889	Intermediate Similarity	NPC84271
0.7889	Intermediate Similarity	NPC275740
0.7889	Intermediate Similarity	NPC77168
0.7882	Intermediate Similarity	NPC474956
0.7882	Intermediate Similarity	NPC267517
0.7872	Intermediate Similarity	NPC292133
0.7872	Intermediate Similarity	NPC43747
0.7865	Intermediate Similarity	NPC474684
0.7865	Intermediate Similarity	NPC96496
0.7865	Intermediate Similarity	NPC142361
0.7849	Intermediate Similarity	NPC184848
0.7849	Intermediate Similarity	NPC69548
0.7849	Intermediate Similarity	NPC48330
0.7841	Intermediate Similarity	NPC98270
0.7841	Intermediate Similarity	NPC474971
0.7841	Intermediate Similarity	NPC474083
0.7841	Intermediate Similarity	NPC478127
0.7835	Intermediate Similarity	NPC33973
0.7835	Intermediate Similarity	NPC70967
0.7831	Intermediate Similarity	NPC899
0.7826	Intermediate Similarity	NPC469315
0.7826	Intermediate Similarity	NPC66429
0.7826	Intermediate Similarity	NPC470224
0.7826	Intermediate Similarity	NPC243866
0.7826	Intermediate Similarity	NPC152897
0.7816	Intermediate Similarity	NPC476082
0.7816	Intermediate Similarity	NPC168188
0.7816	Intermediate Similarity	NPC278648
0.7816	Intermediate Similarity	NPC470015
0.7802	Intermediate Similarity	NPC328141
0.7802	Intermediate Similarity	NPC44240
0.7802	Intermediate Similarity	NPC469400
0.7802	Intermediate Similarity	NPC477149
0.7802	Intermediate Similarity	NPC183283
0.7802	Intermediate Similarity	NPC477147
0.7791	Intermediate Similarity	NPC477372
0.7789	Intermediate Similarity	NPC197386
0.7789	Intermediate Similarity	NPC10364
0.7789	Intermediate Similarity	NPC176845
0.7778	Intermediate Similarity	NPC183546
0.7778	Intermediate Similarity	NPC53911
0.7778	Intermediate Similarity	NPC80335
0.7778	Intermediate Similarity	NPC294480
0.7766	Intermediate Similarity	NPC322063
0.7766	Intermediate Similarity	NPC173272
0.7766	Intermediate Similarity	NPC120708
0.7755	Intermediate Similarity	NPC135854
0.7755	Intermediate Similarity	NPC470251
0.7755	Intermediate Similarity	NPC119493
0.7755	Intermediate Similarity	NPC216245
0.7755	Intermediate Similarity	NPC223741
0.7755	Intermediate Similarity	NPC2436
0.7753	Intermediate Similarity	NPC91525
0.7753	Intermediate Similarity	NPC89077
0.7753	Intermediate Similarity	NPC9892
0.7753	Intermediate Similarity	NPC329943
0.7753	Intermediate Similarity	NPC212843
0.7753	Intermediate Similarity	NPC72133
0.7753	Intermediate Similarity	NPC10005
0.7753	Intermediate Similarity	NPC244174
0.7753	Intermediate Similarity	NPC220478
0.7753	Intermediate Similarity	NPC56588
0.7742	Intermediate Similarity	NPC303863
0.7742	Intermediate Similarity	NPC294266
0.7742	Intermediate Similarity	NPC159410
0.7742	Intermediate Similarity	NPC240617
0.7738	Intermediate Similarity	NPC472300
0.7732	Intermediate Similarity	NPC473928
0.7732	Intermediate Similarity	NPC271266
0.7732	Intermediate Similarity	NPC308351
0.7732	Intermediate Similarity	NPC119601
0.7732	Intermediate Similarity	NPC308726
0.7727	Intermediate Similarity	NPC171789
0.7727	Intermediate Similarity	NPC209882
0.7727	Intermediate Similarity	NPC214043
0.7727	Intermediate Similarity	NPC82902
0.7727	Intermediate Similarity	NPC59453

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 NPC109512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1932
0.2-0.3	4326
0.3-0.4	1814
0.4-0.5	466
0.5-0.6	157
0.6-0.7	172
0.7-0.8	95
0.8-0.85	6
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8391	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7521	Approved
0.8372	Intermediate Similarity	NPD6409	Approved
0.8372	Intermediate Similarity	NPD5330	Approved
0.8372	Intermediate Similarity	NPD7334	Approved
0.8372	Intermediate Similarity	NPD6684	Approved
0.8372	Intermediate Similarity	NPD7146	Approved
0.8182	Intermediate Similarity	NPD6672	Approved
0.8182	Intermediate Similarity	NPD6903	Approved
0.8182	Intermediate Similarity	NPD5737	Approved
0.8022	Intermediate Similarity	NPD6399	Phase 3
0.7955	Intermediate Similarity	NPD6098	Approved
0.7727	Intermediate Similarity	NPD4786	Approved
0.7717	Intermediate Similarity	NPD6050	Approved
0.7692	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD6904	Approved
0.7692	Intermediate Similarity	NPD6080	Approved
0.7692	Intermediate Similarity	NPD6673	Approved
0.7667	Intermediate Similarity	NPD3573	Approved
0.766	Intermediate Similarity	NPD5695	Phase 3
0.7609	Intermediate Similarity	NPD5207	Approved
0.7609	Intermediate Similarity	NPD5692	Phase 3
0.7582	Intermediate Similarity	NPD5208	Approved
0.7561	Intermediate Similarity	NPD5777	Approved
0.7527	Intermediate Similarity	NPD6079	Approved
0.7527	Intermediate Similarity	NPD5694	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7474	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4692	Approved
0.7386	Intermediate Similarity	NPD4139	Approved
0.7368	Intermediate Similarity	NPD7900	Approved
0.7368	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5279	Phase 3
0.7353	Intermediate Similarity	NPD7320	Approved
0.7353	Intermediate Similarity	NPD6899	Approved
0.7353	Intermediate Similarity	NPD6881	Approved
0.734	Intermediate Similarity	NPD8035	Phase 2
0.734	Intermediate Similarity	NPD5693	Phase 1
0.734	Intermediate Similarity	NPD8034	Phase 2
0.734	Intermediate Similarity	NPD6411	Approved
0.7333	Intermediate Similarity	NPD3668	Phase 3
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD3666	Approved
0.7327	Intermediate Similarity	NPD6008	Approved
0.7294	Intermediate Similarity	NPD3702	Approved
0.7292	Intermediate Similarity	NPD5654	Approved
0.7282	Intermediate Similarity	NPD6373	Approved
0.7282	Intermediate Similarity	NPD6372	Approved
0.7255	Intermediate Similarity	NPD5701	Approved
0.7255	Intermediate Similarity	NPD5697	Approved
0.7245	Intermediate Similarity	NPD5696	Approved
0.7241	Intermediate Similarity	NPD3617	Approved
0.7212	Intermediate Similarity	NPD7102	Approved
0.7212	Intermediate Similarity	NPD6883	Approved
0.7212	Intermediate Similarity	NPD7290	Approved
0.7188	Intermediate Similarity	NPD6001	Approved
0.7184	Intermediate Similarity	NPD6011	Approved
0.7176	Intermediate Similarity	NPD5733	Approved
0.7174	Intermediate Similarity	NPD3618	Phase 1
0.7158	Intermediate Similarity	NPD7515	Phase 2
0.7158	Intermediate Similarity	NPD5281	Approved
0.7158	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD5959	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6051	Approved
0.7128	Intermediate Similarity	NPD6101	Approved
0.7115	Intermediate Similarity	NPD6014	Approved
0.7115	Intermediate Similarity	NPD6013	Approved
0.7115	Intermediate Similarity	NPD6012	Approved
0.7111	Intermediate Similarity	NPD4221	Approved
0.7111	Intermediate Similarity	NPD4223	Phase 3
0.7075	Intermediate Similarity	NPD6882	Approved
0.7075	Intermediate Similarity	NPD8297	Approved
0.7065	Intermediate Similarity	NPD5329	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5222	Approved
0.7041	Intermediate Similarity	NPD5221	Approved
0.7041	Intermediate Similarity	NPD4697	Phase 3
0.7041	Intermediate Similarity	NPD7732	Phase 3
0.7024	Intermediate Similarity	NPD4747	Approved
0.6989	Remote Similarity	NPD5280	Approved
0.6989	Remote Similarity	NPD4694	Approved
0.6989	Remote Similarity	NPD5690	Phase 2
0.6977	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4687	Approved
0.697	Remote Similarity	NPD5173	Approved
0.697	Remote Similarity	NPD4755	Approved
0.6957	Remote Similarity	NPD4197	Approved
0.6947	Remote Similarity	NPD4753	Phase 2
0.6947	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5276	Approved
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6412	Phase 2
0.6907	Remote Similarity	NPD4202	Approved
0.6905	Remote Similarity	NPD4137	Phase 3
0.6881	Remote Similarity	NPD6868	Approved
0.6848	Remote Similarity	NPD4788	Approved
0.6832	Remote Similarity	NPD4696	Approved
0.6832	Remote Similarity	NPD5286	Approved
0.6832	Remote Similarity	NPD4700	Approved
0.6832	Remote Similarity	NPD5285	Approved
0.6824	Remote Similarity	NPD4691	Approved
0.6818	Remote Similarity	NPD6117	Approved
0.6809	Remote Similarity	NPD4138	Approved
0.6809	Remote Similarity	NPD5205	Approved
0.6809	Remote Similarity	NPD4688	Approved
0.6809	Remote Similarity	NPD4690	Approved
0.6809	Remote Similarity	NPD4693	Phase 3
0.6809	Remote Similarity	NPD4689	Approved
0.6796	Remote Similarity	NPD6052	Approved
0.6792	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5223	Approved
0.6757	Remote Similarity	NPD6335	Approved
0.6747	Remote Similarity	NPD4224	Phase 2
0.6744	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6081	Approved
0.6744	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6116	Phase 1
0.6739	Remote Similarity	NPD6435	Approved
0.6733	Remote Similarity	NPD7638	Approved
0.6727	Remote Similarity	NPD6274	Approved
0.6705	Remote Similarity	NPD7339	Approved
0.6705	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD7614	Phase 1
0.6699	Remote Similarity	NPD5225	Approved
0.6699	Remote Similarity	NPD5211	Phase 2
0.6699	Remote Similarity	NPD5224	Approved
0.6699	Remote Similarity	NPD5226	Approved
0.6699	Remote Similarity	NPD4633	Approved
0.6697	Remote Similarity	NPD7094	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6697	Remote Similarity	NPD6858	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5174	Approved
0.6635	Remote Similarity	NPD5175	Approved
0.6635	Remote Similarity	NPD4754	Approved
0.6632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4789	Approved
0.6628	Remote Similarity	NPD4245	Approved
0.6628	Remote Similarity	NPD4244	Approved
0.6627	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6313	Approved
0.6607	Remote Similarity	NPD6314	Approved
0.6604	Remote Similarity	NPD6614	Approved
0.66	Remote Similarity	NPD5210	Approved
0.66	Remote Similarity	NPD4629	Approved
0.6591	Remote Similarity	NPD4058	Approved
0.6579	Remote Similarity	NPD6909	Approved
0.6579	Remote Similarity	NPD6908	Approved
0.6571	Remote Similarity	NPD5141	Approved
0.6566	Remote Similarity	NPD5778	Approved
0.6566	Remote Similarity	NPD5133	Approved
0.6566	Remote Similarity	NPD5779	Approved
0.6538	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4096	Approved
0.6522	Remote Similarity	NPD5368	Approved
0.6522	Remote Similarity	NPD4748	Discontinued
0.6518	Remote Similarity	NPD6009	Approved
0.6517	Remote Similarity	NPD3703	Phase 2
0.6517	Remote Similarity	NPD8039	Approved
0.6512	Remote Similarity	NPD3698	Phase 2
0.6512	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4767	Approved
0.6509	Remote Similarity	NPD4768	Approved
0.6505	Remote Similarity	NPD6404	Discontinued
0.6491	Remote Similarity	NPD6319	Approved
0.6466	Remote Similarity	NPD7604	Phase 2
0.6455	Remote Similarity	NPD6053	Discontinued
0.6444	Remote Similarity	NPD3701	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