NPASS Compound

Structure

CID61411 OpenBabel06191715392D 34 40 0 0 1 0 0 0 0 0999 V2000 2.6596 -0.4958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4898 -0.7703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9980 -6.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8637 -5.8709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6303 -1.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6311 -4.4281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3148 -5.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4730 -4.8857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8384 -3.9128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9971 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4721 -1.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3140 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9466 -0.5154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 -1.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9485 -3.4285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1558 -2.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7878 -1.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4882 -0.6642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 -2.4572 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1564 -4.8852 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4727 -3.9138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8387 -4.8847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7887 -1.9710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9854 0.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9977 -5.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6305 -2.4567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6308 -3.4281 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1561 -3.9133 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3143 -3.4276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1062 -1.0016 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7049 -5.3843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3958 1.1283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1070 -1.9725 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 2 18 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 28 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 30 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 16 29 1 0 0 0 0 17 1 1 1 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 15 1 1 0 0 0 19 23 1 0 0 0 0 19 33 1 0 0 0 0 20 25 1 0 0 0 0 20 28 1 6 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 26 1 6 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 26 27 1 6 0 0 0 27 6 1 1 0 0 0 28 29 1 1 0 0 0 29 12 1 1 0 0 0 30 13 1 1 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.31
Volume:	494.792
LogP:	5.647
LogD:	4.629
LogS:	-5.415
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	6.232
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:	-5.176
MDCK Permeability:	2.2384772819350474e-05
Pgp-inhibitor:	0.753
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.485
30% Bioavailability (F30%):	0.594

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	92.81243133544922%
Volume Distribution (VD):	1.231
Pgp-substrate:	4.4273481369018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.806
CYP2C19-inhibitor:	0.326
CYP2C19-substrate:	0.926
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.835

ADMET: Excretion

Clearance (CL):	9.94
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.744
Human Hepatotoxicity (H-HT):	0.435
Drug-inuced Liver Injury (DILI):	0.33
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.953
Carcinogencity:	0.377
Eye Corrosion:	0.01
Eye Irritation:	0.056
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC61411

Natural Product ID:	NPC61411
*Common Name:**	Pseudolarolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ULWBDUNMGKITLY-JCWARNQUSA-N
Standard InCHI:	InChI=1S/C30H42O4/c1-17-13-30(14-18(2)24(32)34-30)33-19-15-27(6)21-8-7-20-25(3,4)22(31)9-10-28(20)16-29(21,28)12-11-26(27,5)23(17)19/h14,17,19-21,23H,7-13,15-16H2,1-6H3/t17-,19-,20+,21+,23+,26-,27+,28-,29+,30+/m1/s1
SMILES:	C[C@@H]1C[C@]2(C=C(C)C(=O)O2)O[C@@H]2C[C@@]3(C)[C@@H]4CC[C@H]5C(C)(C)C(=O)CC[C@]65C[C@@]46CC[C@]3(C)[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463567
PubChem CID:	21592337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346966]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	leaves,?stems	USA	n.a.	PMID[16124770]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760078]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	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
EC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	EC50	=	0.79	ug.mL-1	PMID[505673]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	0.67	ug.mL-1	PMID[505673]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	0.73	ug.mL-1	PMID[505673]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.49	ug.mL-1	PMID[505673]

☑ 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 NPC61411 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	279
0.1-0.2	1678
0.2-0.3	5680
0.3-0.4	12893
0.4-0.5	8381
0.5-0.6	6769
0.6-0.7	5896
0.7-0.8	1093
0.8-0.85	27
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8529	High Similarity	NPC187159
0.8491	Intermediate Similarity	NPC127790
0.8333	Intermediate Similarity	NPC33473
0.8257	Intermediate Similarity	NPC475030
0.8252	Intermediate Similarity	NPC111684
0.8252	Intermediate Similarity	NPC58052
0.8235	Intermediate Similarity	NPC477722
0.8224	Intermediate Similarity	NPC476764
0.8224	Intermediate Similarity	NPC476763
0.8182	Intermediate Similarity	NPC179642
0.8174	Intermediate Similarity	NPC470312
0.8155	Intermediate Similarity	NPC281134
0.8148	Intermediate Similarity	NPC476761
0.8148	Intermediate Similarity	NPC476762
0.8148	Intermediate Similarity	NPC470309
0.8148	Intermediate Similarity	NPC476760
0.8142	Intermediate Similarity	NPC268213
0.812	Intermediate Similarity	NPC27363
0.8095	Intermediate Similarity	NPC98868
0.8095	Intermediate Similarity	NPC252295
0.8067	Intermediate Similarity	NPC287423
0.8058	Intermediate Similarity	NPC304968
0.8058	Intermediate Similarity	NPC128488
0.8053	Intermediate Similarity	NPC471398
0.8051	Intermediate Similarity	NPC32868
0.8051	Intermediate Similarity	NPC241456
0.8037	Intermediate Similarity	NPC476769
0.802	Intermediate Similarity	NPC285982
0.8019	Intermediate Similarity	NPC201406
0.7983	Intermediate Similarity	NPC469750
0.7983	Intermediate Similarity	NPC250556
0.7981	Intermediate Similarity	NPC280877
0.7981	Intermediate Similarity	NPC476174
0.7966	Intermediate Similarity	NPC204812
0.7963	Intermediate Similarity	NPC112009
0.7963	Intermediate Similarity	NPC221421
0.7963	Intermediate Similarity	NPC180204
0.7961	Intermediate Similarity	NPC475657
0.7961	Intermediate Similarity	NPC475700
0.7946	Intermediate Similarity	NPC470311
0.7944	Intermediate Similarity	NPC268829
0.7944	Intermediate Similarity	NPC25177
0.7944	Intermediate Similarity	NPC475099
0.7944	Intermediate Similarity	NPC222875
0.7944	Intermediate Similarity	NPC310981
0.7944	Intermediate Similarity	NPC295110
0.7944	Intermediate Similarity	NPC247701
0.7928	Intermediate Similarity	NPC112457
0.7928	Intermediate Similarity	NPC476759
0.7925	Intermediate Similarity	NPC153792
0.7925	Intermediate Similarity	NPC271387
0.7917	Intermediate Similarity	NPC117702
0.7917	Intermediate Similarity	NPC471356
0.7917	Intermediate Similarity	NPC471357
0.7917	Intermediate Similarity	NPC240070
0.7917	Intermediate Similarity	NPC146456
0.7917	Intermediate Similarity	NPC469757
0.7917	Intermediate Similarity	NPC179412
0.7917	Intermediate Similarity	NPC329784
0.7913	Intermediate Similarity	NPC290693
0.7909	Intermediate Similarity	NPC471601
0.7905	Intermediate Similarity	NPC325960
0.7905	Intermediate Similarity	NPC307164
0.7905	Intermediate Similarity	NPC319692
0.79	Intermediate Similarity	NPC195640
0.7895	Intermediate Similarity	NPC471633
0.7895	Intermediate Similarity	NPC84949
0.7895	Intermediate Similarity	NPC69576
0.7895	Intermediate Similarity	NPC31354
0.789	Intermediate Similarity	NPC228669
0.789	Intermediate Similarity	NPC164835
0.7885	Intermediate Similarity	NPC294266
0.7864	Intermediate Similarity	NPC221282
0.7864	Intermediate Similarity	NPC218301
0.7851	Intermediate Similarity	NPC311534
0.785	Intermediate Similarity	NPC477716
0.785	Intermediate Similarity	NPC476767
0.785	Intermediate Similarity	NPC470906
0.785	Intermediate Similarity	NPC251680
0.785	Intermediate Similarity	NPC477721
0.7845	Intermediate Similarity	NPC113448
0.7843	Intermediate Similarity	NPC177141
0.7838	Intermediate Similarity	NPC219900
0.7838	Intermediate Similarity	NPC470269
0.7838	Intermediate Similarity	NPC392
0.7838	Intermediate Similarity	NPC177524
0.783	Intermediate Similarity	NPC204054
0.783	Intermediate Similarity	NPC476768
0.783	Intermediate Similarity	NPC257726
0.783	Intermediate Similarity	NPC476253
0.7826	Intermediate Similarity	NPC5311
0.7826	Intermediate Similarity	NPC193382
0.7826	Intermediate Similarity	NPC199428
0.7826	Intermediate Similarity	NPC310341
0.7826	Intermediate Similarity	NPC72772
0.7826	Intermediate Similarity	NPC196931
0.7826	Intermediate Similarity	NPC99620
0.7826	Intermediate Similarity	NPC469794
0.781	Intermediate Similarity	NPC293052
0.78	Intermediate Similarity	NPC323765
0.78	Intermediate Similarity	NPC189311
0.7798	Intermediate Similarity	NPC196471
0.7798	Intermediate Similarity	NPC10232
0.7798	Intermediate Similarity	NPC97487
0.7798	Intermediate Similarity	NPC160583
0.7798	Intermediate Similarity	NPC189588
0.7798	Intermediate Similarity	NPC187302
0.7798	Intermediate Similarity	NPC254202
0.7797	Intermediate Similarity	NPC470418
0.7787	Intermediate Similarity	NPC469753
0.7787	Intermediate Similarity	NPC9499
0.7787	Intermediate Similarity	NPC276838
0.7787	Intermediate Similarity	NPC469751
0.7787	Intermediate Similarity	NPC284406
0.7787	Intermediate Similarity	NPC89514
0.7787	Intermediate Similarity	NPC471358
0.7787	Intermediate Similarity	NPC469755
0.7787	Intermediate Similarity	NPC180079
0.7787	Intermediate Similarity	NPC471361
0.7787	Intermediate Similarity	NPC219085
0.7787	Intermediate Similarity	NPC125077
0.7787	Intermediate Similarity	NPC232785
0.7787	Intermediate Similarity	NPC91
0.7787	Intermediate Similarity	NPC197707
0.7787	Intermediate Similarity	NPC10823
0.7787	Intermediate Similarity	NPC251866
0.7787	Intermediate Similarity	NPC140092
0.7787	Intermediate Similarity	NPC17896
0.7787	Intermediate Similarity	NPC471360
0.7787	Intermediate Similarity	NPC469752
0.7787	Intermediate Similarity	NPC471359
0.7787	Intermediate Similarity	NPC6108
0.7787	Intermediate Similarity	NPC471352
0.7787	Intermediate Similarity	NPC86159
0.7787	Intermediate Similarity	NPC188234
0.7787	Intermediate Similarity	NPC329986
0.7787	Intermediate Similarity	NPC469754
0.7787	Intermediate Similarity	NPC70542
0.7778	Intermediate Similarity	NPC474327
0.7778	Intermediate Similarity	NPC477717
0.7778	Intermediate Similarity	NPC474179
0.7778	Intermediate Similarity	NPC475834
0.7778	Intermediate Similarity	NPC170862
0.7767	Intermediate Similarity	NPC273199
0.7767	Intermediate Similarity	NPC8062
0.7759	Intermediate Similarity	NPC87250
0.7759	Intermediate Similarity	NPC93883
0.7759	Intermediate Similarity	NPC471353
0.7759	Intermediate Similarity	NPC474418
0.7759	Intermediate Similarity	NPC27507
0.7759	Intermediate Similarity	NPC84987
0.7759	Intermediate Similarity	NPC244402
0.7759	Intermediate Similarity	NPC158344
0.7759	Intermediate Similarity	NPC473852
0.7759	Intermediate Similarity	NPC243196
0.7759	Intermediate Similarity	NPC142066
0.7759	Intermediate Similarity	NPC471351
0.7759	Intermediate Similarity	NPC196429
0.7759	Intermediate Similarity	NPC309034
0.7759	Intermediate Similarity	NPC34390
0.7759	Intermediate Similarity	NPC152615
0.7759	Intermediate Similarity	NPC157376
0.7759	Intermediate Similarity	NPC77319
0.7759	Intermediate Similarity	NPC471354
0.7759	Intermediate Similarity	NPC471355
0.7759	Intermediate Similarity	NPC99728
0.7759	Intermediate Similarity	NPC50305
0.7757	Intermediate Similarity	NPC176845
0.7745	Intermediate Similarity	NPC226863
0.7745	Intermediate Similarity	NPC28227
0.7739	Intermediate Similarity	NPC477580
0.7736	Intermediate Similarity	NPC322063
0.7736	Intermediate Similarity	NPC29152
0.7731	Intermediate Similarity	NPC470419
0.7727	Intermediate Similarity	NPC189616
0.7724	Intermediate Similarity	NPC16569
0.7724	Intermediate Similarity	NPC253456
0.7724	Intermediate Similarity	NPC159338
0.7723	Intermediate Similarity	NPC470051
0.7723	Intermediate Similarity	NPC261253
0.7723	Intermediate Similarity	NPC474045
0.7723	Intermediate Similarity	NPC470050
0.7719	Intermediate Similarity	NPC470063
0.7714	Intermediate Similarity	NPC84893
0.7712	Intermediate Similarity	NPC281840
0.7706	Intermediate Similarity	NPC308351
0.7706	Intermediate Similarity	NPC22388
0.7706	Intermediate Similarity	NPC271266
0.77	Intermediate Similarity	NPC475100
0.7699	Intermediate Similarity	NPC163314
0.7699	Intermediate Similarity	NPC476766
0.7699	Intermediate Similarity	NPC16270
0.7699	Intermediate Similarity	NPC472666
0.7692	Intermediate Similarity	NPC470420
0.7692	Intermediate Similarity	NPC470113
0.7692	Intermediate Similarity	NPC290651
0.7692	Intermediate Similarity	NPC239293
0.7692	Intermediate Similarity	NPC473720
0.7692	Intermediate Similarity	NPC475913
0.7692	Intermediate Similarity	NPC83287

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 NPC61411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1808
0.2-0.3	4086
0.3-0.4	2070
0.4-0.5	513
0.5-0.6	214
0.6-0.7	174
0.7-0.8	44
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
0.81	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD7507	Approved
0.7925	Intermediate Similarity	NPD7638	Approved
0.7921	Intermediate Similarity	NPD6903	Approved
0.79	Intermediate Similarity	NPD6684	Approved
0.79	Intermediate Similarity	NPD7334	Approved
0.79	Intermediate Similarity	NPD7146	Approved
0.79	Intermediate Similarity	NPD7521	Approved
0.79	Intermediate Similarity	NPD6409	Approved
0.79	Intermediate Similarity	NPD5330	Approved
0.785	Intermediate Similarity	NPD7639	Approved
0.785	Intermediate Similarity	NPD7640	Approved
0.7838	Intermediate Similarity	NPD6686	Approved
0.781	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7319	Approved
0.7748	Intermediate Similarity	NPD6412	Phase 2
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD5693	Phase 1
0.7692	Intermediate Similarity	NPD7328	Approved
0.7677	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6008	Approved
0.7627	Intermediate Similarity	NPD7516	Approved
0.7573	Intermediate Similarity	NPD5737	Approved
0.7573	Intermediate Similarity	NPD6672	Approved
0.7563	Intermediate Similarity	NPD8377	Approved
0.7563	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7383	Intermediate Similarity	NPD6001	Approved
0.7339	Intermediate Similarity	NPD6083	Phase 2
0.7339	Intermediate Similarity	NPD6084	Phase 2
0.7333	Intermediate Similarity	NPD6051	Approved
0.728	Intermediate Similarity	NPD7736	Approved
0.7265	Intermediate Similarity	NPD6882	Approved
0.7238	Intermediate Similarity	NPD5208	Approved
0.7232	Intermediate Similarity	NPD7632	Discontinued
0.7213	Intermediate Similarity	NPD7503	Approved
0.7212	Intermediate Similarity	NPD6098	Approved
0.7196	Intermediate Similarity	NPD6050	Approved
0.7177	Intermediate Similarity	NPD7492	Approved
0.7167	Intermediate Similarity	NPD7115	Discovery
0.7167	Intermediate Similarity	NPD6009	Approved
0.7156	Intermediate Similarity	NPD5695	Phase 3
0.7131	Intermediate Similarity	NPD6054	Approved
0.713	Intermediate Similarity	NPD6399	Phase 3
0.712	Intermediate Similarity	NPD6616	Approved
0.7119	Intermediate Similarity	NPD6053	Discontinued
0.7117	Intermediate Similarity	NPD5696	Approved
0.7103	Intermediate Similarity	NPD5692	Phase 3
0.7103	Intermediate Similarity	NPD5207	Approved
0.7069	Intermediate Similarity	NPD6881	Approved
0.7069	Intermediate Similarity	NPD6899	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7748	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7078	Approved
0.7059	Intermediate Similarity	NPD8133	Approved
0.7043	Intermediate Similarity	NPD6675	Approved
0.7043	Intermediate Similarity	NPD6402	Approved
0.7043	Intermediate Similarity	NPD7128	Approved
0.7043	Intermediate Similarity	NPD5739	Approved
0.7037	Intermediate Similarity	NPD5694	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3133	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.7016	Intermediate Similarity	NPD6370	Approved
0.6992	Remote Similarity	NPD6059	Approved
0.6983	Remote Similarity	NPD5697	Approved
0.696	Remote Similarity	NPD7604	Phase 2
0.6952	Remote Similarity	NPD1694	Approved
0.6949	Remote Similarity	NPD7290	Approved
0.6949	Remote Similarity	NPD7102	Approved
0.6949	Remote Similarity	NPD6883	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6935	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD8293	Discontinued
0.6923	Remote Similarity	NPD6011	Approved
0.6917	Remote Similarity	NPD4632	Approved
0.6891	Remote Similarity	NPD6869	Approved
0.6891	Remote Similarity	NPD6649	Approved
0.6891	Remote Similarity	NPD6617	Approved
0.6891	Remote Similarity	NPD6650	Approved
0.6891	Remote Similarity	NPD8130	Phase 1
0.6891	Remote Similarity	NPD6847	Approved
0.6881	Remote Similarity	NPD7515	Phase 2
0.688	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD5959	Approved
0.6875	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD6052	Approved
0.6864	Remote Similarity	NPD6013	Approved
0.6864	Remote Similarity	NPD6014	Approved
0.6864	Remote Similarity	NPD6373	Approved
0.6864	Remote Similarity	NPD6372	Approved
0.6864	Remote Similarity	NPD6012	Approved
0.6852	Remote Similarity	NPD4753	Phase 2
0.6838	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5701	Approved
0.6833	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD4221	Approved
0.6822	Remote Similarity	NPD3573	Approved
0.6807	Remote Similarity	NPD6371	Approved
0.6792	Remote Similarity	NPD5329	Approved
0.6789	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD4788	Approved
0.675	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5284	Approved
0.6727	Remote Similarity	NPD6079	Approved
0.6727	Remote Similarity	NPD8034	Phase 2
0.6727	Remote Similarity	NPD5281	Approved
0.6727	Remote Similarity	NPD8035	Phase 2
0.6723	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6319	Approved
0.6698	Remote Similarity	NPD4197	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.6697	Remote Similarity	NPD5328	Approved
0.6697	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD5654	Approved
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6695	Remote Similarity	NPD6614	Approved
0.6693	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD6858	Approved
0.6639	Remote Similarity	NPD7094	Approved
0.6638	Remote Similarity	NPD5211	Phase 2
0.6636	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6033	Approved
0.6609	Remote Similarity	NPD5286	Approved
0.6609	Remote Similarity	NPD4696	Approved
0.6609	Remote Similarity	NPD5285	Approved
0.6589	Remote Similarity	NPD6336	Discontinued
0.6579	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD5690	Phase 2
0.6574	Remote Similarity	NPD4690	Approved
0.6574	Remote Similarity	NPD4689	Approved
0.6574	Remote Similarity	NPD4693	Phase 3
0.6574	Remote Similarity	NPD4138	Approved
0.6574	Remote Similarity	NPD4688	Approved
0.6574	Remote Similarity	NPD3618	Phase 1
0.6574	Remote Similarity	NPD5205	Approved
0.6562	Remote Similarity	NPD8328	Phase 3
0.656	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD3668	Phase 3
0.6532	Remote Similarity	NPD6274	Approved
0.6525	Remote Similarity	NPD5141	Approved
0.6515	Remote Similarity	NPD5956	Approved
0.6509	Remote Similarity	NPD3667	Approved
0.6508	Remote Similarity	NPD7100	Approved
0.6508	Remote Similarity	NPD7101	Approved
0.6496	Remote Similarity	NPD5226	Approved
0.6496	Remote Similarity	NPD4633	Approved
0.6496	Remote Similarity	NPD5225	Approved
0.6496	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD5222	Approved
0.6491	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7732	Phase 3
0.6491	Remote Similarity	NPD5221	Approved
0.6489	Remote Similarity	NPD8337	Approved
0.6489	Remote Similarity	NPD8336	Approved
0.6486	Remote Similarity	NPD6698	Approved
0.6486	Remote Similarity	NPD46	Approved
0.648	Remote Similarity	NPD6317	Approved
0.6466	Remote Similarity	NPD4700	Approved
0.6449	Remote Similarity	NPD5362	Discontinued
0.6446	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5174	Approved
0.6441	Remote Similarity	NPD5175	Approved
0.6435	Remote Similarity	NPD5173	Approved
0.6429	Remote Similarity	NPD6313	Approved
0.6429	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD5279	Phase 3
0.6422	Remote Similarity	NPD4694	Approved
0.6422	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5280	Approved
0.6417	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4691	Approved
0.64	Remote Similarity	NPD4747	Approved
0.64	Remote Similarity	NPD6868	Approved
0.6396	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4634	Approved
0.6381	Remote Similarity	NPD4195	Approved
0.6379	Remote Similarity	NPD4225	Approved
0.6348	Remote Similarity	NPD4697	Phase 3
0.6343	Remote Similarity	NPD7260	Phase 2

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