NPASS Compound

Structure

NPC471608 OpenBabel07101718202D 31 34 0 0 1 0 0 0 0 0999 V2000 3.4641 -5.0000 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 0.8660 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 2.5981 -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 1.7321 0.0000 0.0000 C 0 0 0 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 -0.8660 -1.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 6 9 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 27 1 0 0 0 0 14 28 2 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 22 2 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 1 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 1 0 0 0 22 31 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 6 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	448.926
LogP:	3.58
LogD:	3.287
LogS:	-4.062
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	4.383
Fsp3:	0.72
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:	-4.779
MDCK Permeability:	8.277789675048552e-06
Pgp-inhibitor:	0.057
Pgp-substrate:	0.288
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	65.6246566772461%
Volume Distribution (VD):	0.528
Pgp-substrate:	41.56405258178711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.362
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	5.488
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.66
Skin Sensitization:	0.182
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC471608

Natural Product ID:	NPC471608
*Common Name:**	[(3S,4Ar,6As,12Ar,12Bs)-11-Hydroxy-8,9-Bis(Hydroxymethyl)-4,4,6A,12B-Tetramethyl-1,2,3,4A,5,6,12,12A-Octahydrobenzo[A]Xanthen-3-Yl] Acetate
IUPAC Name:	[(3S,4aR,6aS,12aR,12bS)-11-hydroxy-8,9-bis(hydroxymethyl)-4,4,6a,12b-tetramethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthen-3-yl] acetate
Synonyms:
Standard InCHIKey:	RIYSRJBAAXWICD-KOSDUOMESA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-14(28)30-21-7-8-24(4)19(23(21,2)3)6-9-25(5)20(24)11-16-18(29)10-15(12-26)17(13-27)22(16)31-25/h10,19-21,26-27,29H,6-9,11-13H2,1-5H3/t19-,20+,21-,24-,25-/m0/s1
SMILES:	OCc1cc(O)c2c(c1CO)O[C@@]1([C@H](C2)[C@@]2(C)CC[C@@H](C([C@@H]2CC1)(C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL292063
PubChem CID:	44305558
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001828] Isoflavanols

*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
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341709]
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9873488]
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	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	2

Activity Type	# Activity
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	460000.0	nM	PMID[507683]
NPT2	Others	Unspecified		IC50	n.a.	100000.0	nM	PMID[507683]

☑ 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 NPC471608 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	333
0.1-0.2	1463
0.2-0.3	3173
0.3-0.4	6990
0.4-0.5	10556
0.5-0.6	5666
0.6-0.7	8628
0.7-0.8	5540
0.8-0.85	300
0.85-0.9	44
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9448	High Similarity	NPC476452
0.8947	High Similarity	NPC4950
0.8947	High Similarity	NPC239118
0.8936	High Similarity	NPC472800
0.8919	High Similarity	NPC158784
0.8912	High Similarity	NPC212142
0.8859	High Similarity	NPC302915
0.8859	High Similarity	NPC2745
0.8841	High Similarity	NPC472797
0.8836	High Similarity	NPC472457
0.8836	High Similarity	NPC90645
0.8819	High Similarity	NPC138149
0.88	High Similarity	NPC325860
0.88	High Similarity	NPC157783
0.8794	High Similarity	NPC473107
0.8792	High Similarity	NPC195561
0.8792	High Similarity	NPC205501
0.8792	High Similarity	NPC118000
0.8792	High Similarity	NPC162976
0.8786	High Similarity	NPC472798
0.8777	High Similarity	NPC249425
0.8776	High Similarity	NPC475872
0.8767	High Similarity	NPC36732
0.8767	High Similarity	NPC473845
0.8759	High Similarity	NPC20631
0.8759	High Similarity	NPC93640
0.8758	High Similarity	NPC158542
0.8723	High Similarity	NPC469610
0.8714	High Similarity	NPC160623
0.8705	High Similarity	NPC472796
0.8705	High Similarity	NPC472795
0.8701	High Similarity	NPC218818
0.8696	High Similarity	NPC186889
0.8658	High Similarity	NPC473876
0.8652	High Similarity	NPC469611
0.8643	High Similarity	NPC196193
0.8633	High Similarity	NPC38604
0.8633	High Similarity	NPC211179
0.8611	High Similarity	NPC131198
0.8611	High Similarity	NPC306365
0.8608	High Similarity	NPC125465
0.8592	High Similarity	NPC177712
0.8592	High Similarity	NPC24913
0.8591	High Similarity	NPC474397
0.8582	High Similarity	NPC68205
0.8582	High Similarity	NPC181497
0.8582	High Similarity	NPC293203
0.8582	High Similarity	NPC8899
0.8582	High Similarity	NPC271945
0.8582	High Similarity	NPC211413
0.8582	High Similarity	NPC472590
0.8582	High Similarity	NPC118683
0.8582	High Similarity	NPC244888
0.8582	High Similarity	NPC164804
0.8581	High Similarity	NPC475719
0.8581	High Similarity	NPC106126
0.8581	High Similarity	NPC101255
0.8581	High Similarity	NPC108994
0.8581	High Similarity	NPC43716
0.8571	High Similarity	NPC93962
0.8571	High Similarity	NPC96719
0.8571	High Similarity	NPC222108
0.8562	High Similarity	NPC265075
0.8561	High Similarity	NPC473134
0.8551	High Similarity	NPC293801
0.8542	High Similarity	NPC327735
0.8531	High Similarity	NPC97834
0.8531	High Similarity	NPC223008
0.8531	High Similarity	NPC296915
0.8531	High Similarity	NPC225696
0.8531	High Similarity	NPC115335
0.8531	High Similarity	NPC198154
0.8523	High Similarity	NPC215678
0.8523	High Similarity	NPC233980
0.8523	High Similarity	NPC274454
0.8521	High Similarity	NPC13005
0.8521	High Similarity	NPC289624
0.8521	High Similarity	NPC27578
0.8511	High Similarity	NPC27187
0.8511	High Similarity	NPC470225
0.85	High Similarity	NPC53986
0.85	High Similarity	NPC38664
0.85	High Similarity	NPC274717
0.8491	Intermediate Similarity	NPC472621
0.8477	Intermediate Similarity	NPC295573
0.8477	Intermediate Similarity	NPC181452
0.8477	Intermediate Similarity	NPC470208
0.8477	Intermediate Similarity	NPC220006
0.8477	Intermediate Similarity	NPC146388
0.8467	Intermediate Similarity	NPC174251
0.8467	Intermediate Similarity	NPC153182
0.8462	Intermediate Similarity	NPC185777
0.8462	Intermediate Similarity	NPC211352
0.8462	Intermediate Similarity	NPC472617
0.8462	Intermediate Similarity	NPC469965
0.8462	Intermediate Similarity	NPC77196
0.8456	Intermediate Similarity	NPC469701
0.8456	Intermediate Similarity	NPC469557
0.8451	Intermediate Similarity	NPC129106
0.8451	Intermediate Similarity	NPC207892
0.8451	Intermediate Similarity	NPC268917
0.8451	Intermediate Similarity	NPC164574
0.8451	Intermediate Similarity	NPC118114
0.8451	Intermediate Similarity	NPC129784
0.8451	Intermediate Similarity	NPC12875
0.8451	Intermediate Similarity	NPC196765
0.8451	Intermediate Similarity	NPC206224
0.8451	Intermediate Similarity	NPC228369
0.8451	Intermediate Similarity	NPC17343
0.8451	Intermediate Similarity	NPC300875
0.8451	Intermediate Similarity	NPC476166
0.8451	Intermediate Similarity	NPC236014
0.8451	Intermediate Similarity	NPC280653
0.8451	Intermediate Similarity	NPC150011
0.8442	Intermediate Similarity	NPC472799
0.8442	Intermediate Similarity	NPC268484
0.844	Intermediate Similarity	NPC16577
0.8438	Intermediate Similarity	NPC472622
0.8435	Intermediate Similarity	NPC5155
0.8431	Intermediate Similarity	NPC160196
0.8429	Intermediate Similarity	NPC66331
0.8425	Intermediate Similarity	NPC32630
0.8425	Intermediate Similarity	NPC144512
0.8425	Intermediate Similarity	NPC137262
0.8425	Intermediate Similarity	NPC47040
0.8425	Intermediate Similarity	NPC470209
0.8425	Intermediate Similarity	NPC279573
0.8425	Intermediate Similarity	NPC37428
0.8425	Intermediate Similarity	NPC475836
0.8425	Intermediate Similarity	NPC278600
0.8425	Intermediate Similarity	NPC35501
0.8421	Intermediate Similarity	NPC183380
0.8421	Intermediate Similarity	NPC241636
0.8414	Intermediate Similarity	NPC126101
0.8414	Intermediate Similarity	NPC141717
0.8414	Intermediate Similarity	NPC471522
0.8411	Intermediate Similarity	NPC474834
0.8411	Intermediate Similarity	NPC303013
0.8411	Intermediate Similarity	NPC117788
0.8411	Intermediate Similarity	NPC474856
0.8411	Intermediate Similarity	NPC290902
0.8411	Intermediate Similarity	NPC159697
0.8411	Intermediate Similarity	NPC130959
0.8411	Intermediate Similarity	NPC95990
0.8411	Intermediate Similarity	NPC142863
0.8411	Intermediate Similarity	NPC474940
0.8411	Intermediate Similarity	NPC291326
0.8411	Intermediate Similarity	NPC474795
0.8403	Intermediate Similarity	NPC131950
0.8397	Intermediate Similarity	NPC272196
0.8389	Intermediate Similarity	NPC473108
0.838	Intermediate Similarity	NPC470727
0.8378	Intermediate Similarity	NPC186033
0.8377	Intermediate Similarity	NPC223720
0.8369	Intermediate Similarity	NPC223912
0.8367	Intermediate Similarity	NPC213607
0.8367	Intermediate Similarity	NPC174787
0.8367	Intermediate Similarity	NPC182509
0.8357	Intermediate Similarity	NPC50315
0.8357	Intermediate Similarity	NPC276212
0.8357	Intermediate Similarity	NPC26879
0.8357	Intermediate Similarity	NPC230479
0.8357	Intermediate Similarity	NPC283049
0.8357	Intermediate Similarity	NPC82299
0.8356	Intermediate Similarity	NPC470307
0.8356	Intermediate Similarity	NPC470308
0.8355	Intermediate Similarity	NPC475940
0.8355	Intermediate Similarity	NPC474893
0.8354	Intermediate Similarity	NPC177100
0.8354	Intermediate Similarity	NPC139540
0.8345	Intermediate Similarity	NPC125579
0.8345	Intermediate Similarity	NPC15109
0.8345	Intermediate Similarity	NPC11727
0.8333	Intermediate Similarity	NPC85435
0.8333	Intermediate Similarity	NPC92805
0.8333	Intermediate Similarity	NPC142563
0.8333	Intermediate Similarity	NPC141822
0.8333	Intermediate Similarity	NPC57199
0.8333	Intermediate Similarity	NPC241165
0.8333	Intermediate Similarity	NPC86069
0.8333	Intermediate Similarity	NPC1220
0.8333	Intermediate Similarity	NPC205797
0.8333	Intermediate Similarity	NPC291551
0.8333	Intermediate Similarity	NPC31849
0.8333	Intermediate Similarity	NPC477674
0.8333	Intermediate Similarity	NPC165483
0.8333	Intermediate Similarity	NPC4547
0.8323	Intermediate Similarity	NPC80918
0.8323	Intermediate Similarity	NPC188578
0.8322	Intermediate Similarity	NPC103799
0.8322	Intermediate Similarity	NPC153019
0.8322	Intermediate Similarity	NPC282508
0.8312	Intermediate Similarity	NPC48671
0.8311	Intermediate Similarity	NPC472523
0.8311	Intermediate Similarity	NPC71046
0.8311	Intermediate Similarity	NPC287286
0.8311	Intermediate Similarity	NPC35216
0.8311	Intermediate Similarity	NPC195357
0.8311	Intermediate Similarity	NPC152771
0.831	Intermediate Similarity	NPC134360

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 NPC471608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	900
0.2-0.3	1718
0.3-0.4	2627
0.4-0.5	1915
0.5-0.6	1051
0.6-0.7	542
0.7-0.8	125
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD6410	Clinical (unspecified phase)
0.8511	High Similarity	NPD4907	Clinical (unspecified phase)
0.8503	High Similarity	NPD6398	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD4625	Phase 3
0.8369	Intermediate Similarity	NPD4908	Phase 1
0.8356	Intermediate Similarity	NPD6100	Approved
0.8356	Intermediate Similarity	NPD6099	Approved
0.8333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5124	Phase 1
0.8273	Intermediate Similarity	NPD4749	Approved
0.8227	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4140	Approved
0.8067	Intermediate Similarity	NPD6674	Discontinued
0.8049	Intermediate Similarity	NPD5844	Phase 1
0.8014	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD1610	Phase 2
0.7958	Intermediate Similarity	NPD6696	Suspended
0.7947	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD37	Approved
0.7901	Intermediate Similarity	NPD6959	Discontinued
0.7891	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1613	Approved
0.7879	Intermediate Similarity	NPD7228	Approved
0.7875	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD4966	Approved
0.7875	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD7819	Suspended
0.7834	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD5762	Approved
0.7815	Intermediate Similarity	NPD5763	Approved
0.7793	Intermediate Similarity	NPD2861	Phase 2
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7229	Phase 3
0.7736	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4626	Approved
0.7718	Intermediate Similarity	NPD5735	Approved
0.7702	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7671	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3750	Approved
0.766	Intermediate Similarity	NPD5691	Approved
0.7654	Intermediate Similarity	NPD7768	Phase 2
0.7654	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5327	Phase 3
0.7622	Intermediate Similarity	NPD422	Phase 1
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7097	Phase 1
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7571	Intermediate Similarity	NPD7340	Approved
0.7568	Intermediate Similarity	NPD3027	Phase 3
0.7568	Intermediate Similarity	NPD7095	Approved
0.7551	Intermediate Similarity	NPD5736	Approved
0.755	Intermediate Similarity	NPD4097	Suspended
0.755	Intermediate Similarity	NPD6353	Approved
0.7532	Intermediate Similarity	NPD6273	Approved
0.7532	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6232	Discontinued
0.7518	Intermediate Similarity	NPD7644	Approved
0.7517	Intermediate Similarity	NPD7985	Registered
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD1611	Approved
0.75	Intermediate Similarity	NPD7075	Discontinued
0.7485	Intermediate Similarity	NPD7240	Approved
0.7484	Intermediate Similarity	NPD1652	Phase 2
0.7483	Intermediate Similarity	NPD1778	Approved
0.747	Intermediate Similarity	NPD8127	Discontinued
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7467	Intermediate Similarity	NPD8032	Phase 2
0.7466	Intermediate Similarity	NPD8651	Approved
0.7438	Intermediate Similarity	NPD1653	Approved
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7436	Intermediate Similarity	NPD7003	Approved
0.7423	Intermediate Similarity	NPD8455	Phase 2
0.7423	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3620	Phase 2
0.74	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD8312	Approved
0.7397	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6559	Discontinued
0.7376	Intermediate Similarity	NPD6671	Approved
0.7358	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7447	Phase 1
0.7357	Intermediate Similarity	NPD1398	Phase 1
0.7355	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6004	Phase 3
0.7355	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6005	Phase 3
0.7355	Intermediate Similarity	NPD6002	Phase 3
0.7351	Intermediate Similarity	NPD6663	Approved
0.7349	Intermediate Similarity	NPD5709	Phase 3
0.7347	Intermediate Similarity	NPD1283	Approved
0.7346	Intermediate Similarity	NPD4380	Phase 2
0.7342	Intermediate Similarity	NPD6666	Approved
0.7342	Intermediate Similarity	NPD6667	Approved
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD3748	Approved
0.7337	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3496	Discontinued
0.7305	Intermediate Similarity	NPD4666	Phase 3
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2979	Phase 3
0.7297	Intermediate Similarity	NPD3094	Phase 2
0.7296	Intermediate Similarity	NPD7213	Phase 3
0.7296	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7212	Phase 2
0.7296	Intermediate Similarity	NPD7041	Phase 2
0.7289	Intermediate Similarity	NPD3749	Approved
0.7284	Intermediate Similarity	NPD3226	Approved
0.7284	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.725	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4624	Approved
0.7244	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2346	Discontinued
0.7241	Intermediate Similarity	NPD7549	Discontinued
0.7239	Intermediate Similarity	NPD6599	Discontinued
0.7235	Intermediate Similarity	NPD6166	Phase 2
0.7235	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7741	Discontinued
0.7222	Intermediate Similarity	NPD3091	Approved
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7219	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD5710	Approved
0.7215	Intermediate Similarity	NPD3892	Phase 2
0.7215	Intermediate Similarity	NPD7466	Approved
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1549	Phase 2
0.7194	Intermediate Similarity	NPD4750	Phase 3
0.719	Intermediate Similarity	NPD2238	Phase 2
0.7188	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2797	Approved
0.7179	Intermediate Similarity	NPD2935	Discontinued
0.7179	Intermediate Similarity	NPD1551	Phase 2
0.7179	Intermediate Similarity	NPD2438	Suspended
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7172	Intermediate Similarity	NPD5585	Approved
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7163	Intermediate Similarity	NPD5535	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD3092	Approved
0.7143	Intermediate Similarity	NPD1091	Approved
0.7134	Intermediate Similarity	NPD7266	Discontinued
0.7133	Intermediate Similarity	NPD7157	Approved
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7054	Approved
0.7108	Intermediate Similarity	NPD5929	Approved
0.7107	Intermediate Similarity	NPD8166	Discontinued
0.7107	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4110	Phase 3
0.7101	Intermediate Similarity	NPD6746	Phase 2
0.7101	Intermediate Similarity	NPD5494	Approved
0.7097	Intermediate Similarity	NPD6653	Approved
0.7095	Intermediate Similarity	NPD1608	Approved
0.7089	Intermediate Similarity	NPD2424	Discontinued
0.7079	Intermediate Similarity	NPD4663	Approved
0.707	Intermediate Similarity	NPD4477	Approved
0.707	Intermediate Similarity	NPD4476	Approved
0.7069	Intermediate Similarity	NPD7472	Approved
0.7066	Intermediate Similarity	NPD5402	Approved
0.7065	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD7294	Phase 1
0.7055	Intermediate Similarity	NPD7427	Discontinued
0.7052	Intermediate Similarity	NPD3751	Discontinued
0.7051	Intermediate Similarity	NPD4538	Approved
0.7051	Intermediate Similarity	NPD4536	Approved
0.7051	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2800	Approved
0.7039	Intermediate Similarity	NPD7906	Approved
0.7037	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4481	Phase 3
0.7019	Intermediate Similarity	NPD5058	Phase 3
0.7018	Intermediate Similarity	NPD3051	Approved
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7007	Intermediate Similarity	NPD3095	Discontinued
0.7006	Intermediate Similarity	NPD4578	Approved
0.7006	Intermediate Similarity	NPD7312	Approved
0.7006	Intermediate Similarity	NPD7311	Approved
0.7006	Intermediate Similarity	NPD4577	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