NPASS Compound

Structure

NPC470611 OpenBabel07101718232D 35 39 0 0 1 0 0 0 0 0999 V2000 0.9945 -1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0193 2.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 0.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1418 -0.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8219 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8738 -1.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2757 0.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0078 -0.9932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4097 0.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7398 0.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0078 2.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0678 2.9849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6884 1.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7398 -0.9932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1418 1.5068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1418 0.5068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2757 2.0068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8738 0.5068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8738 1.5068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0733 3.0894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6666 2.1759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 1 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 7.0078 0.0068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4097 1.5068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6059 -1.4932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7398 2.0068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5733 3.9555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 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 16 1 0 0 0 0 2 16 1 0 0 0 0 4 28 1 0 0 0 0 5 28 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 20 1 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 17 3 1 1 0 0 0 17 26 1 0 0 0 0 18 31 1 1 0 0 0 19 14 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 29 1 1 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 32 1 1 0 0 0 24 26 1 0 0 0 0 24 33 1 1 0 0 0 25 12 1 6 0 0 0 25 27 1 0 0 0 0 25 34 1 0 0 0 0 26 30 1 1 0 0 0 27 16 1 6 0 0 0 27 35 1 0 0 0 0 28 34 1 0 0 0 0 28 35 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.38
Volume:	528.605
LogP:	5.291
LogD:	5.053
LogS:	-4.872
# Rotatable Bonds:	4
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	5.195
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.733
MDCK Permeability:	3.130890763713978e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.245

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	91.96267700195312%
Volume Distribution (VD):	1.177
Pgp-substrate:	4.92538595199585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.503

ADMET: Excretion

Clearance (CL):	9.914
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.802
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.656
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.919
Carcinogencity:	0.371
Eye Corrosion:	0.092
Eye Irritation:	0.041
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC470611

Natural Product ID:	NPC470611
*Common Name:**	(3S,5S,6R,8R,9S,10R,13S,14S,16S,17R)-17-((R)-1-((4R,5S)-5-Isopropyl-2,2-Dimethyl-1,3-Dioxolan-4-Yl)Propan-2-Yl)-10,13-Dimethylhexadecahydro-1H-Cyclopenta[A]Phenanthrene-3,6,16-Triol
IUPAC Name:	(3S,5S,6R,8R,9S,10R,13S,14S,16S,17R)-17-[(2R)-1-[(4R,5S)-2,2-dimethyl-5-propan-2-yl-1,3-dioxolan-4-yl]propan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,16-triol
Synonyms:
Standard InCHIKey:	OAINTSYRDOUQHU-GTEDTODYSA-N
Standard InCHI:	InChI=1S/C30H52O5/c1-16(2)27-25(34-28(4,5)35-27)12-17(3)26-24(33)15-21-19-14-23(32)22-13-18(31)8-10-29(22,6)20(19)9-11-30(21,26)7/h16-27,31-33H,8-15H2,1-7H3/t17-,18+,19-,20+,21+,22-,23-,24+,25-,26+,27+,29-,30+/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1)[C@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@@H]([C@@H]2[C@@H](C[C@H]1OC(O[C@H]1C(C)C)(C)C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088124
PubChem CID:	70697393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins 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
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	roots	sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA)	n.a.	PMID[22880631]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3.5	ug.mL-1	PMID[527390]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4.3	ug.mL-1	PMID[527390]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[527390]
NPT1524	Cell Line	MM96L	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[527390]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	8.5	ug.mL-1	PMID[527390]
NPT1523	Cell Line	NFF	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[527390]

☑ 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 NPC470611 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	448
0.1-0.2	4220
0.2-0.3	13754
0.3-0.4	10809
0.4-0.5	5262
0.5-0.6	4804
0.6-0.7	2355
0.7-0.8	793
0.8-0.85	190
0.85-0.9	49
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC296734
0.9383	High Similarity	NPC161928
0.9383	High Similarity	NPC210658
0.9375	High Similarity	NPC273290
0.9375	High Similarity	NPC232044
0.9268	High Similarity	NPC128475
0.925	High Similarity	NPC227260
0.9231	High Similarity	NPC7479
0.9231	High Similarity	NPC257296
0.9231	High Similarity	NPC248944
0.9157	High Similarity	NPC20822
0.9125	High Similarity	NPC470070
0.9048	High Similarity	NPC473542
0.8941	High Similarity	NPC149966
0.8941	High Similarity	NPC5632
0.8941	High Similarity	NPC59006
0.8929	High Similarity	NPC228059
0.8846	High Similarity	NPC64081
0.8846	High Similarity	NPC474574
0.8837	High Similarity	NPC167644
0.8837	High Similarity	NPC149400
0.8837	High Similarity	NPC256104
0.8837	High Similarity	NPC122083
0.8837	High Similarity	NPC211845
0.8837	High Similarity	NPC311246
0.8837	High Similarity	NPC182740
0.8837	High Similarity	NPC144790
0.8837	High Similarity	NPC88962
0.881	High Similarity	NPC281004
0.8795	High Similarity	NPC471240
0.8765	High Similarity	NPC475388
0.8736	High Similarity	NPC30687
0.8736	High Similarity	NPC175
0.8736	High Similarity	NPC174024
0.8736	High Similarity	NPC477224
0.8736	High Similarity	NPC312678
0.8736	High Similarity	NPC291547
0.8736	High Similarity	NPC252253
0.8736	High Similarity	NPC473851
0.8736	High Similarity	NPC3538
0.8736	High Similarity	NPC179859
0.8736	High Similarity	NPC24960
0.8736	High Similarity	NPC131693
0.8736	High Similarity	NPC45959
0.8736	High Similarity	NPC473774
0.8736	High Similarity	NPC475436
0.8736	High Similarity	NPC253268
0.8736	High Similarity	NPC113500
0.8706	High Similarity	NPC473472
0.8706	High Similarity	NPC82955
0.8706	High Similarity	NPC102725
0.8675	High Similarity	NPC290612
0.8636	High Similarity	NPC473067
0.8636	High Similarity	NPC473064
0.8636	High Similarity	NPC473065
0.8636	High Similarity	NPC21897
0.8625	High Similarity	NPC81074
0.8625	High Similarity	NPC477282
0.8621	High Similarity	NPC234352
0.8621	High Similarity	NPC249204
0.8621	High Similarity	NPC297348
0.8621	High Similarity	NPC48339
0.8621	High Similarity	NPC177834
0.8621	High Similarity	NPC477547
0.8621	High Similarity	NPC250393
0.8621	High Similarity	NPC141769
0.8621	High Similarity	NPC477451
0.8621	High Similarity	NPC325828
0.8608	High Similarity	NPC11907
0.8608	High Similarity	NPC133596
0.8605	High Similarity	NPC223143
0.8605	High Similarity	NPC65550
0.8605	High Similarity	NPC279329
0.859	High Similarity	NPC91387
0.859	High Similarity	NPC270306
0.859	High Similarity	NPC231680
0.8571	High Similarity	NPC470610
0.8553	High Similarity	NPC251201
0.8553	High Similarity	NPC232925
0.8553	High Similarity	NPC63588
0.8539	High Similarity	NPC139271
0.8539	High Similarity	NPC142264
0.8539	High Similarity	NPC476728
0.8539	High Similarity	NPC121453
0.8539	High Similarity	NPC304011
0.8539	High Similarity	NPC156377
0.8539	High Similarity	NPC476510
0.8523	High Similarity	NPC294686
0.8523	High Similarity	NPC222731
0.8523	High Similarity	NPC217205
0.8523	High Similarity	NPC471464
0.8523	High Similarity	NPC264101
0.8523	High Similarity	NPC291203
0.8506	High Similarity	NPC307167
0.8506	High Similarity	NPC473830
0.8506	High Similarity	NPC204881
0.8506	High Similarity	NPC473637
0.8506	High Similarity	NPC210759
0.8506	High Similarity	NPC476668
0.8506	High Similarity	NPC36372
0.8506	High Similarity	NPC229801
0.8506	High Similarity	NPC293609
0.8471	Intermediate Similarity	NPC140446
0.8471	Intermediate Similarity	NPC43912
0.8471	Intermediate Similarity	NPC472396
0.8462	Intermediate Similarity	NPC48795
0.8444	Intermediate Similarity	NPC475207
0.8444	Intermediate Similarity	NPC477222
0.8444	Intermediate Similarity	NPC233649
0.8444	Intermediate Similarity	NPC477223
0.8444	Intermediate Similarity	NPC476112
0.8444	Intermediate Similarity	NPC307534
0.8444	Intermediate Similarity	NPC470028
0.8442	Intermediate Similarity	NPC187471
0.8442	Intermediate Similarity	NPC470071
0.8442	Intermediate Similarity	NPC1340
0.8442	Intermediate Similarity	NPC252182
0.8434	Intermediate Similarity	NPC477285
0.8434	Intermediate Similarity	NPC111582
0.8427	Intermediate Similarity	NPC6295
0.8427	Intermediate Similarity	NPC19400
0.8427	Intermediate Similarity	NPC107188
0.8427	Intermediate Similarity	NPC473610
0.8427	Intermediate Similarity	NPC107962
0.8427	Intermediate Similarity	NPC211354
0.8427	Intermediate Similarity	NPC475351
0.8427	Intermediate Similarity	NPC206003
0.8427	Intermediate Similarity	NPC474399
0.8427	Intermediate Similarity	NPC473727
0.8421	Intermediate Similarity	NPC477820
0.8409	Intermediate Similarity	NPC137004
0.8409	Intermediate Similarity	NPC473726
0.8409	Intermediate Similarity	NPC172838
0.8409	Intermediate Similarity	NPC277774
0.8409	Intermediate Similarity	NPC476669
0.8395	Intermediate Similarity	NPC476176
0.8375	Intermediate Similarity	NPC476233
0.8354	Intermediate Similarity	NPC317242
0.8353	Intermediate Similarity	NPC155531
0.8353	Intermediate Similarity	NPC215968
0.8352	Intermediate Similarity	NPC292775
0.8352	Intermediate Similarity	NPC473638
0.8352	Intermediate Similarity	NPC473518
0.8352	Intermediate Similarity	NPC473616
0.8333	Intermediate Similarity	NPC116756
0.8333	Intermediate Similarity	NPC128572
0.8333	Intermediate Similarity	NPC287483
0.8333	Intermediate Similarity	NPC103616
0.8333	Intermediate Similarity	NPC84111
0.8333	Intermediate Similarity	NPC195297
0.8333	Intermediate Similarity	NPC184617
0.8333	Intermediate Similarity	NPC475643
0.8333	Intermediate Similarity	NPC98018
0.8333	Intermediate Similarity	NPC132080
0.8333	Intermediate Similarity	NPC153719
0.8333	Intermediate Similarity	NPC470863
0.8333	Intermediate Similarity	NPC473601
0.8333	Intermediate Similarity	NPC470866
0.8333	Intermediate Similarity	NPC470865
0.8333	Intermediate Similarity	NPC97700
0.8333	Intermediate Similarity	NPC30856
0.8333	Intermediate Similarity	NPC475625
0.8333	Intermediate Similarity	NPC160426
0.8333	Intermediate Similarity	NPC470864
0.8333	Intermediate Similarity	NPC232037
0.8333	Intermediate Similarity	NPC284104
0.8333	Intermediate Similarity	NPC474156
0.8315	Intermediate Similarity	NPC475325
0.8315	Intermediate Similarity	NPC309866
0.8315	Intermediate Similarity	NPC473503
0.8315	Intermediate Similarity	NPC305418
0.8313	Intermediate Similarity	NPC286719
0.8313	Intermediate Similarity	NPC477286
0.8295	Intermediate Similarity	NPC473066
0.8276	Intermediate Similarity	NPC131466
0.8272	Intermediate Similarity	NPC471045
0.8261	Intermediate Similarity	NPC470030
0.825	Intermediate Similarity	NPC163597
0.8242	Intermediate Similarity	NPC51520
0.8242	Intermediate Similarity	NPC470862
0.8242	Intermediate Similarity	NPC83137
0.8242	Intermediate Similarity	NPC470861
0.8242	Intermediate Similarity	NPC274200
0.8242	Intermediate Similarity	NPC232611
0.8242	Intermediate Similarity	NPC303069
0.8242	Intermediate Similarity	NPC115165
0.8235	Intermediate Similarity	NPC266651
0.8228	Intermediate Similarity	NPC304499
0.8222	Intermediate Similarity	NPC469710
0.8222	Intermediate Similarity	NPC305808
0.8222	Intermediate Similarity	NPC92196
0.8202	Intermediate Similarity	NPC161035
0.8193	Intermediate Similarity	NPC190940
0.8182	Intermediate Similarity	NPC66407
0.8172	Intermediate Similarity	NPC476512
0.8172	Intermediate Similarity	NPC472081
0.8172	Intermediate Similarity	NPC475574
0.8172	Intermediate Similarity	NPC108227
0.8172	Intermediate Similarity	NPC477225
0.8171	Intermediate Similarity	NPC477287

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 NPC470611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	4248
0.2-0.3	3178
0.3-0.4	682
0.4-0.5	279
0.5-0.6	234
0.6-0.7	80
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD6928	Phase 2
0.8621	High Similarity	NPD8171	Discontinued
0.7826	Intermediate Similarity	NPD7991	Discontinued
0.7732	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6115	Approved
0.7412	Intermediate Similarity	NPD6118	Approved
0.7412	Intermediate Similarity	NPD6114	Approved
0.7412	Intermediate Similarity	NPD6697	Approved
0.7407	Intermediate Similarity	NPD4787	Phase 1
0.7294	Intermediate Similarity	NPD6116	Phase 1
0.7176	Intermediate Similarity	NPD6117	Approved
0.7143	Intermediate Similarity	NPD1810	Approved
0.7143	Intermediate Similarity	NPD1811	Approved
0.6941	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7327	Approved
0.6881	Remote Similarity	NPD7328	Approved
0.686	Remote Similarity	NPD3703	Phase 2
0.6854	Remote Similarity	NPD7525	Registered
0.6818	Remote Similarity	NPD7516	Approved
0.6786	Remote Similarity	NPD4244	Approved
0.6786	Remote Similarity	NPD2686	Approved
0.6786	Remote Similarity	NPD4245	Approved
0.6786	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2687	Approved
0.6786	Remote Similarity	NPD2254	Approved
0.6757	Remote Similarity	NPD6059	Approved
0.6757	Remote Similarity	NPD8377	Approved
0.6757	Remote Similarity	NPD6054	Approved
0.6757	Remote Similarity	NPD8294	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6370	Approved
0.6571	Remote Similarity	NPD6412	Phase 2
0.6549	Remote Similarity	NPD6016	Approved
0.6549	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD7492	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.6512	Remote Similarity	NPD5777	Approved
0.6496	Remote Similarity	NPD7736	Approved
0.6491	Remote Similarity	NPD5988	Approved
0.6477	Remote Similarity	NPD3702	Approved
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6466	Remote Similarity	NPD6616	Approved
0.6466	Remote Similarity	NPD7507	Approved
0.6463	Remote Similarity	NPD371	Approved
0.6452	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3669	Approved
0.6435	Remote Similarity	NPD6067	Discontinued
0.6429	Remote Similarity	NPD8034	Phase 2
0.6429	Remote Similarity	NPD8035	Phase 2
0.641	Remote Similarity	NPD7078	Approved
0.641	Remote Similarity	NPD8293	Discontinued
0.6408	Remote Similarity	NPD1700	Approved
0.6396	Remote Similarity	NPD6940	Discontinued
0.6395	Remote Similarity	NPD4789	Approved
0.6356	Remote Similarity	NPD6033	Approved
0.6355	Remote Similarity	NPD8174	Phase 2
0.6353	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5360	Phase 3
0.6346	Remote Similarity	NPD7632	Discontinued
0.6339	Remote Similarity	NPD6009	Approved
0.6327	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6700	Approved
0.6316	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7319	Approved
0.6263	Remote Similarity	NPD6703	Approved
0.6263	Remote Similarity	NPD6702	Approved
0.6261	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD8308	Discontinued
0.6222	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6081	Approved
0.6129	Remote Similarity	NPD4748	Discontinued
0.6126	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD6942	Approved
0.6111	Remote Similarity	NPD7339	Approved
0.6087	Remote Similarity	NPD3671	Phase 1
0.6071	Remote Similarity	NPD4632	Approved
0.6055	Remote Similarity	NPD7320	Approved
0.6042	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7645	Phase 2
0.602	Remote Similarity	NPD7524	Approved
0.602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6008	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD8418	Phase 2
0.5982	Remote Similarity	NPD8297	Approved
0.5977	Remote Similarity	NPD6705	Phase 1
0.5955	Remote Similarity	NPD4758	Discontinued
0.5938	Remote Similarity	NPD4788	Approved
0.5938	Remote Similarity	NPD6695	Phase 3
0.593	Remote Similarity	NPD4224	Phase 2
0.5914	Remote Similarity	NPD5364	Discontinued
0.5913	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6881	Approved
0.5909	Remote Similarity	NPD6899	Approved
0.5897	Remote Similarity	NPD6319	Approved
0.5895	Remote Similarity	NPD1779	Approved
0.5895	Remote Similarity	NPD1780	Approved
0.5887	Remote Similarity	NPD8449	Approved
0.5882	Remote Similarity	NPD4202	Approved
0.5882	Remote Similarity	NPD6399	Phase 3
0.5882	Remote Similarity	NPD7604	Phase 2
0.5856	Remote Similarity	NPD6372	Approved
0.5856	Remote Similarity	NPD6373	Approved
0.5847	Remote Similarity	NPD5983	Phase 2
0.584	Remote Similarity	NPD8450	Suspended
0.5818	Remote Similarity	NPD5701	Approved
0.5818	Remote Similarity	NPD5697	Approved
0.581	Remote Similarity	NPD4755	Approved
0.5804	Remote Similarity	NPD7290	Approved
0.5804	Remote Similarity	NPD7102	Approved
0.5804	Remote Similarity	NPD6883	Approved
0.5802	Remote Similarity	NPD2267	Suspended
0.5794	Remote Similarity	NPD4159	Approved
0.5785	Remote Similarity	NPD6336	Discontinued
0.578	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4243	Approved
0.5766	Remote Similarity	NPD6686	Approved
0.5766	Remote Similarity	NPD6011	Approved
0.5766	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6650	Approved
0.5752	Remote Similarity	NPD6617	Approved
0.5752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6869	Approved
0.5752	Remote Similarity	NPD8130	Phase 1
0.5752	Remote Similarity	NPD6649	Approved
0.5752	Remote Similarity	NPD6847	Approved
0.5745	Remote Similarity	NPD4238	Approved
0.5745	Remote Similarity	NPD4802	Phase 2
0.5743	Remote Similarity	NPD5328	Approved
0.5726	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5701	Remote Similarity	NPD5285	Approved
0.5701	Remote Similarity	NPD4700	Approved
0.5701	Remote Similarity	NPD5286	Approved
0.5701	Remote Similarity	NPD4696	Approved
0.57	Remote Similarity	NPD7750	Discontinued
0.5699	Remote Similarity	NPD6933	Approved
0.5684	Remote Similarity	NPD6929	Approved
0.5676	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4634	Approved
0.566	Remote Similarity	NPD7920	Phase 3
0.566	Remote Similarity	NPD7919	Phase 3
0.566	Remote Similarity	NPD6084	Phase 2
0.566	Remote Similarity	NPD6083	Phase 2
0.5658	Remote Similarity	NPD385	Approved
0.5658	Remote Similarity	NPD384	Approved
0.5652	Remote Similarity	NPD6926	Approved
0.5652	Remote Similarity	NPD4784	Approved
0.5652	Remote Similarity	NPD4785	Approved
0.5652	Remote Similarity	NPD6924	Approved
0.5648	Remote Similarity	NPD5223	Approved
0.5631	Remote Similarity	NPD6079	Approved
0.5625	Remote Similarity	NPD6931	Approved
0.5625	Remote Similarity	NPD6930	Phase 2
0.562	Remote Similarity	NPD8328	Phase 3
0.5619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD8088	Phase 1
0.56	Remote Similarity	NPD3618	Phase 1

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