NPASS Compound

Structure

CID105495 OpenBabel06191715452D 35 39 0 0 1 0 0 0 0 0999 V2000 0.8484 -3.4160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5382 -3.4150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2375 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7330 0.5908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6686 1.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.9525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5372 -1.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3829 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5378 2.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8466 -2.4411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6930 -2.9277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6923 0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 -1.9521 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5374 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5370 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3831 2.9288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3831 0.9766 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6920 -0.0004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8461 -0.4876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2285 2.4408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2285 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5378 1.4647 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 -0.4880 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8464 -1.4645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1086 -2.6444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5371 -1.4884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2439 0.2200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 3.9379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1023 2.9453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 29 1 0 0 0 0 10 11 1 0 0 0 0 10 28 1 0 0 0 0 11 30 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 27 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 1 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 24 1 0 0 0 0 20 33 1 6 0 0 0 21 25 1 0 0 0 0 21 34 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 28 1 6 0 0 0 24 29 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 35 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	525.968
LogP:	4.134
LogD:	3.933
LogS:	-4.296
# Rotatable Bonds:	2
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	5.485
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:	-5.043
MDCK Permeability:	3.960753929277416e-06
Pgp-inhibitor:	0.029
Pgp-substrate:	0.238
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.163
30% Bioavailability (F30%):	0.63

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	88.15442657470703%
Volume Distribution (VD):	0.818
Pgp-substrate:	7.537260055541992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	5.03
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.698
Maximum Recommended Daily Dose:	0.606
Skin Sensitization:	0.579
Carcinogencity:	0.048
Eye Corrosion:	0.168
Eye Irritation:	0.109
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC105495

Natural Product ID:	NPC105495
*Common Name:**	Rubiarbonol F
IUPAC Name:	(1R,3S,3aR,5aS,5bS,6S,7aR,9R,10R,11aS,13aR,13bR)-3a-(hydroxymethyl)-5a,8,8,11a,13a-pentamethyl-3-propan-2-yl-1,2,3,4,5,5b,6,7,7a,9,10,11,13,13b-tetradecahydrocyclopenta[a]chrysene-1,6,9,10-tetrol
Synonyms:	Rubiarbonol F
Standard InCHIKey:	KJXUHHARWYEHNL-ZEUDKGLNSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-16(2)18-12-20(33)24-29(7)9-8-17-23(28(29,6)10-11-30(18,24)15-31)19(32)13-22-26(3,4)25(35)21(34)14-27(17,22)5/h8,16,18-25,31-35H,9-15H2,1-7H3/t18-,19-,20+,21+,22-,23-,24+,25-,27+,28-,29+,30+/m0/s1
SMILES:	CC(C)[C@@H]1C[C@H]([C@@H]2[C@@]3(C)CC=C4[C@@H]([C@H](C[C@H]5C(C)(C)[C@H]([C@@H](C[C@]45C)O)O)O)[C@]3(C)CC[C@@]12CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469280
PubChem CID:	21582935
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
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350148]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762798]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21044847]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	root	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	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
Others	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	15.4	%	PMID[479351]
NPT2	Others	Unspecified	Inhibition	=	7.9	%	PMID[479351]
NPT2	Others	Unspecified	Inhibition	=	9.6	%	PMID[479351]
NPT2	Others	Unspecified	Inhibition	=	22.0	%	PMID[479351]
NPT2	Others	Unspecified	Inhibition	=	60.4	%	PMID[479351]

☑ 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 NPC105495 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	193
0.1-0.2	1600
0.2-0.3	5979
0.3-0.4	15035
0.4-0.5	8326
0.5-0.6	4676
0.6-0.7	4536
0.7-0.8	2043
0.8-0.85	229
0.85-0.9	59
0.9-0.95	19
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC24277
0.9412	High Similarity	NPC475664
0.9398	High Similarity	NPC124172
0.9398	High Similarity	NPC209802
0.9294	High Similarity	NPC474657
0.9294	High Similarity	NPC186145
0.9277	High Similarity	NPC110778
0.9195	High Similarity	NPC475751
0.9195	High Similarity	NPC473956
0.9186	High Similarity	NPC470542
0.9167	High Similarity	NPC255882
0.9167	High Similarity	NPC127606
0.9167	High Similarity	NPC475798
0.9157	High Similarity	NPC470614
0.9157	High Similarity	NPC1272
0.908	High Similarity	NPC109744
0.9048	High Similarity	NPC193870
0.9048	High Similarity	NPC477818
0.9048	High Similarity	NPC207013
0.9048	High Similarity	NPC141941
0.9036	High Similarity	NPC474531
0.9022	High Similarity	NPC208358
0.8977	High Similarity	NPC107189
0.8966	High Similarity	NPC474668
0.8953	High Similarity	NPC121981
0.8953	High Similarity	NPC201273
0.8953	High Similarity	NPC94462
0.8953	High Similarity	NPC237344
0.8929	High Similarity	NPC248886
0.8925	High Similarity	NPC155974
0.8916	High Similarity	NPC236112
0.8916	High Similarity	NPC71535
0.8916	High Similarity	NPC78545
0.8916	High Similarity	NPC26117
0.8851	High Similarity	NPC470620
0.8851	High Similarity	NPC271967
0.8804	High Similarity	NPC475033
0.8804	High Similarity	NPC475032
0.8795	High Similarity	NPC1319
0.875	High Similarity	NPC133588
0.875	High Similarity	NPC2158
0.8736	High Similarity	NPC269058
0.8736	High Similarity	NPC6605
0.8736	High Similarity	NPC71520
0.8736	High Similarity	NPC139724
0.8721	High Similarity	NPC238992
0.8706	High Similarity	NPC30166
0.8706	High Similarity	NPC7988
0.8696	High Similarity	NPC253115
0.8696	High Similarity	NPC304899
0.869	High Similarity	NPC236237
0.869	High Similarity	NPC13554
0.869	High Similarity	NPC287749
0.869	High Similarity	NPC102253
0.869	High Similarity	NPC322313
0.8675	High Similarity	NPC87604
0.8675	High Similarity	NPC6978
0.8675	High Similarity	NPC477522
0.8675	High Similarity	NPC167037
0.8675	High Similarity	NPC477817
0.8675	High Similarity	NPC138621
0.8675	High Similarity	NPC477819
0.8675	High Similarity	NPC244385
0.8667	High Similarity	NPC41554
0.8667	High Similarity	NPC97404
0.8652	High Similarity	NPC470361
0.8605	High Similarity	NPC211135
0.8605	High Similarity	NPC85095
0.8605	High Similarity	NPC216420
0.8605	High Similarity	NPC317458
0.8605	High Similarity	NPC159168
0.8605	High Similarity	NPC253402
0.8605	High Similarity	NPC232023
0.8602	High Similarity	NPC190554
0.8588	High Similarity	NPC470383
0.8571	High Similarity	NPC472463
0.8571	High Similarity	NPC98193
0.8571	High Similarity	NPC328714
0.8571	High Similarity	NPC80530
0.8571	High Similarity	NPC273410
0.8556	High Similarity	NPC204188
0.8556	High Similarity	NPC329596
0.8556	High Similarity	NPC80561
0.8556	High Similarity	NPC3345
0.8556	High Similarity	NPC291484
0.8556	High Similarity	NPC11216
0.8554	High Similarity	NPC130136
0.8539	High Similarity	NPC67872
0.8523	High Similarity	NPC152808
0.8523	High Similarity	NPC6391
0.8523	High Similarity	NPC293287
0.8523	High Similarity	NPC261266
0.8523	High Similarity	NPC477604
0.8506	High Similarity	NPC185568
0.8488	Intermediate Similarity	NPC47763
0.8488	Intermediate Similarity	NPC20853
0.8488	Intermediate Similarity	NPC201852
0.8471	Intermediate Similarity	NPC47149
0.8471	Intermediate Similarity	NPC22403
0.8462	Intermediate Similarity	NPC210268
0.8452	Intermediate Similarity	NPC285761
0.8452	Intermediate Similarity	NPC275910
0.8452	Intermediate Similarity	NPC102708
0.8444	Intermediate Similarity	NPC259875
0.8444	Intermediate Similarity	NPC187785
0.8434	Intermediate Similarity	NPC107059
0.8434	Intermediate Similarity	NPC300324
0.8434	Intermediate Similarity	NPC240604
0.8434	Intermediate Similarity	NPC96319
0.8434	Intermediate Similarity	NPC237460
0.8434	Intermediate Similarity	NPC274079
0.8434	Intermediate Similarity	NPC321016
0.8434	Intermediate Similarity	NPC321381
0.8434	Intermediate Similarity	NPC477925
0.8434	Intermediate Similarity	NPC189883
0.8421	Intermediate Similarity	NPC15390
0.8409	Intermediate Similarity	NPC318390
0.8404	Intermediate Similarity	NPC476893
0.8404	Intermediate Similarity	NPC477226
0.8391	Intermediate Similarity	NPC113978
0.8391	Intermediate Similarity	NPC474634
0.8387	Intermediate Similarity	NPC476894
0.8372	Intermediate Similarity	NPC209620
0.8372	Intermediate Similarity	NPC23852
0.8353	Intermediate Similarity	NPC24504
0.8351	Intermediate Similarity	NPC475701
0.8333	Intermediate Similarity	NPC318495
0.8333	Intermediate Similarity	NPC202540
0.8333	Intermediate Similarity	NPC280556
0.8333	Intermediate Similarity	NPC477924
0.8333	Intermediate Similarity	NPC471798
0.8333	Intermediate Similarity	NPC198968
0.8333	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC214570
0.8316	Intermediate Similarity	NPC476895
0.8313	Intermediate Similarity	NPC257347
0.8313	Intermediate Similarity	NPC230301
0.8313	Intermediate Similarity	NPC304309
0.8313	Intermediate Similarity	NPC162742
0.8313	Intermediate Similarity	NPC477923
0.8313	Intermediate Similarity	NPC66566
0.8313	Intermediate Similarity	NPC136188
0.8313	Intermediate Similarity	NPC288035
0.8313	Intermediate Similarity	NPC285893
0.8313	Intermediate Similarity	NPC22105
0.8313	Intermediate Similarity	NPC134847
0.8313	Intermediate Similarity	NPC141071
0.8313	Intermediate Similarity	NPC28657
0.8313	Intermediate Similarity	NPC471723
0.8298	Intermediate Similarity	NPC475178
0.8298	Intermediate Similarity	NPC471903
0.8298	Intermediate Similarity	NPC72204
0.8298	Intermediate Similarity	NPC288970
0.8295	Intermediate Similarity	NPC474493
0.8295	Intermediate Similarity	NPC256567
0.8295	Intermediate Similarity	NPC478102
0.828	Intermediate Similarity	NPC127718
0.828	Intermediate Similarity	NPC111015
0.828	Intermediate Similarity	NPC65402
0.828	Intermediate Similarity	NPC477605
0.8276	Intermediate Similarity	NPC50964
0.8276	Intermediate Similarity	NPC101462
0.8265	Intermediate Similarity	NPC474464
0.8261	Intermediate Similarity	NPC275671
0.8256	Intermediate Similarity	NPC475679
0.8242	Intermediate Similarity	NPC477606
0.8235	Intermediate Similarity	NPC65897
0.8235	Intermediate Similarity	NPC472499
0.8235	Intermediate Similarity	NPC85346
0.8235	Intermediate Similarity	NPC472500
0.8235	Intermediate Similarity	NPC22955
0.8235	Intermediate Similarity	NPC473943
0.8235	Intermediate Similarity	NPC474989
0.8235	Intermediate Similarity	NPC302041
0.8235	Intermediate Similarity	NPC42853
0.8235	Intermediate Similarity	NPC474216
0.8235	Intermediate Similarity	NPC475
0.8235	Intermediate Similarity	NPC472502
0.8235	Intermediate Similarity	NPC477514
0.8235	Intermediate Similarity	NPC300499
0.8235	Intermediate Similarity	NPC99168
0.8235	Intermediate Similarity	NPC470396
0.8229	Intermediate Similarity	NPC471242
0.8222	Intermediate Similarity	NPC475313
0.8214	Intermediate Similarity	NPC91573
0.8214	Intermediate Similarity	NPC113733
0.8214	Intermediate Similarity	NPC14112
0.8214	Intermediate Similarity	NPC202642
0.8214	Intermediate Similarity	NPC134330
0.8214	Intermediate Similarity	NPC129165
0.8214	Intermediate Similarity	NPC46160
0.8214	Intermediate Similarity	NPC73875
0.8214	Intermediate Similarity	NPC86305
0.8211	Intermediate Similarity	NPC177818
0.8202	Intermediate Similarity	NPC474349
0.8202	Intermediate Similarity	NPC474189
0.8193	Intermediate Similarity	NPC100334
0.8193	Intermediate Similarity	NPC472503
0.8193	Intermediate Similarity	NPC308440
0.8191	Intermediate Similarity	NPC8774

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 NPC105495 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	1774
0.2-0.3	4423
0.3-0.4	1951
0.4-0.5	388
0.5-0.6	164
0.6-0.7	188
0.7-0.8	79
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD7525	Registered
0.8434	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7339	Approved
0.8313	Intermediate Similarity	NPD6942	Approved
0.8022	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7645	Phase 2
0.7791	Intermediate Similarity	NPD6933	Approved
0.7765	Intermediate Similarity	NPD4784	Approved
0.7765	Intermediate Similarity	NPD4785	Approved
0.7738	Intermediate Similarity	NPD4243	Approved
0.7692	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD4748	Discontinued
0.7634	Intermediate Similarity	NPD7524	Approved
0.7604	Intermediate Similarity	NPD4202	Approved
0.7558	Intermediate Similarity	NPD6924	Approved
0.7558	Intermediate Similarity	NPD6926	Approved
0.7528	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4755	Approved
0.7474	Intermediate Similarity	NPD5328	Approved
0.7473	Intermediate Similarity	NPD3667	Approved
0.7444	Intermediate Similarity	NPD6931	Approved
0.7444	Intermediate Similarity	NPD6930	Phase 2
0.74	Intermediate Similarity	NPD7638	Approved
0.7391	Intermediate Similarity	NPD6695	Phase 3
0.7358	Intermediate Similarity	NPD4634	Approved
0.734	Intermediate Similarity	NPD3618	Phase 1
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD5285	Approved
0.7327	Intermediate Similarity	NPD5286	Approved
0.7327	Intermediate Similarity	NPD4700	Approved
0.7327	Intermediate Similarity	NPD4696	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.7326	Intermediate Similarity	NPD7151	Approved
0.7326	Intermediate Similarity	NPD7152	Approved
0.7326	Intermediate Similarity	NPD7150	Approved
0.732	Intermediate Similarity	NPD6079	Approved
0.7312	Intermediate Similarity	NPD3133	Approved
0.7312	Intermediate Similarity	NPD3665	Phase 1
0.7312	Intermediate Similarity	NPD3666	Approved
0.7303	Intermediate Similarity	NPD6932	Approved
0.7303	Intermediate Similarity	NPD5776	Phase 2
0.7303	Intermediate Similarity	NPD6925	Approved
0.7297	Intermediate Similarity	NPD7516	Approved
0.7294	Intermediate Similarity	NPD6922	Approved
0.7294	Intermediate Similarity	NPD6923	Approved
0.7294	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5275	Approved
0.7273	Intermediate Similarity	NPD4190	Phase 3
0.7255	Intermediate Similarity	NPD5223	Approved
0.7253	Intermediate Similarity	NPD7509	Discontinued
0.7245	Intermediate Similarity	NPD6399	Phase 3
0.7238	Intermediate Similarity	NPD6412	Phase 2
0.7234	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7145	Approved
0.7209	Intermediate Similarity	NPD7143	Approved
0.7209	Intermediate Similarity	NPD7144	Approved
0.7207	Intermediate Similarity	NPD7328	Approved
0.7207	Intermediate Similarity	NPD7327	Approved
0.7184	Intermediate Similarity	NPD5226	Approved
0.7184	Intermediate Similarity	NPD4633	Approved
0.7184	Intermediate Similarity	NPD5211	Phase 2
0.7184	Intermediate Similarity	NPD5225	Approved
0.7184	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD8033	Approved
0.7156	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD6683	Phase 2
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD5174	Approved
0.7115	Intermediate Similarity	NPD5175	Approved
0.7115	Intermediate Similarity	NPD4754	Approved
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD7750	Discontinued
0.708	Intermediate Similarity	NPD8294	Approved
0.708	Intermediate Similarity	NPD8377	Approved
0.7065	Intermediate Similarity	NPD7514	Phase 3
0.7053	Intermediate Similarity	NPD6893	Approved
0.7048	Intermediate Similarity	NPD5141	Approved
0.703	Intermediate Similarity	NPD4697	Phase 3
0.703	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5222	Approved
0.7018	Intermediate Similarity	NPD8296	Approved
0.7018	Intermediate Similarity	NPD8378	Approved
0.7018	Intermediate Similarity	NPD8335	Approved
0.7018	Intermediate Similarity	NPD8380	Approved
0.7018	Intermediate Similarity	NPD8379	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.6989	Remote Similarity	NPD6902	Approved
0.6981	Remote Similarity	NPD4768	Approved
0.6981	Remote Similarity	NPD4767	Approved
0.697	Remote Similarity	NPD8034	Phase 2
0.697	Remote Similarity	NPD8035	Phase 2
0.6961	Remote Similarity	NPD5173	Approved
0.6947	Remote Similarity	NPD3668	Phase 3
0.6944	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD4159	Approved
0.6916	Remote Similarity	NPD5697	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD4223	Phase 3
0.6915	Remote Similarity	NPD4221	Approved
0.6909	Remote Similarity	NPD8297	Approved
0.6882	Remote Similarity	NPD7332	Phase 2
0.6882	Remote Similarity	NPD6928	Phase 2
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD5329	Approved
0.687	Remote Similarity	NPD7503	Approved
0.6852	Remote Similarity	NPD4730	Approved
0.6852	Remote Similarity	NPD4729	Approved
0.6852	Remote Similarity	NPD5128	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6842	Remote Similarity	NPD4788	Approved
0.6837	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7748	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD4787	Phase 1
0.6818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6814	Remote Similarity	NPD6009	Approved
0.6809	Remote Similarity	NPD6898	Phase 1
0.68	Remote Similarity	NPD7087	Discontinued
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD7902	Approved
0.6796	Remote Similarity	NPD6083	Phase 2
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD6014	Approved
0.6783	Remote Similarity	NPD6319	Approved
0.6783	Remote Similarity	NPD6054	Approved
0.6783	Remote Similarity	NPD6059	Approved
0.678	Remote Similarity	NPD7507	Approved
0.6771	Remote Similarity	NPD4197	Approved
0.6768	Remote Similarity	NPD6051	Approved
0.6765	Remote Similarity	NPD5210	Approved
0.6765	Remote Similarity	NPD4629	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6727	Remote Similarity	NPD5249	Phase 3
0.6727	Remote Similarity	NPD5251	Approved
0.6727	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5247	Approved
0.6727	Remote Similarity	NPD5135	Approved
0.6727	Remote Similarity	NPD5250	Approved
0.6727	Remote Similarity	NPD5169	Approved
0.6727	Remote Similarity	NPD5248	Approved
0.6703	Remote Similarity	NPD8264	Approved
0.6698	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6633	Remote Similarity	NPD5330	Approved
0.6633	Remote Similarity	NPD4689	Approved
0.6633	Remote Similarity	NPD7146	Approved
0.6633	Remote Similarity	NPD6409	Approved
0.6633	Remote Similarity	NPD4138	Approved
0.6633	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7521	Approved
0.6633	Remote Similarity	NPD4688	Approved
0.6633	Remote Similarity	NPD4690	Approved
0.6633	Remote Similarity	NPD5279	Phase 3
0.6633	Remote Similarity	NPD4693	Phase 3
0.6633	Remote Similarity	NPD5205	Approved
0.6633	Remote Similarity	NPD6684	Approved
0.6633	Remote Similarity	NPD7334	Approved
0.6612	Remote Similarity	NPD7319	Approved
0.661	Remote Similarity	NPD7604	Phase 2
0.6581	Remote Similarity	NPD6015	Approved
0.6581	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD6016	Approved
0.6571	Remote Similarity	NPD5290	Discontinued
0.6569	Remote Similarity	NPD8171	Discontinued
0.6559	Remote Similarity	NPD6116	Phase 1
0.6555	Remote Similarity	NPD7492	Approved
0.6525	Remote Similarity	NPD5988	Approved
0.6505	Remote Similarity	NPD7900	Approved
0.6505	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4723	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