NPASS Compound

Structure

NPC474971 OpenBabel07101719252D 26 29 0 0 1 0 0 0 0 0999 V2000 4.8363 2.9680 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 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 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 4.1369 1.0000 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 3.5491 0.1910 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 0.8660 1.5000 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 -0.8660 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 1 4 2 0 0 0 0 2 15 1 0 0 0 0 4 16 1 0 0 0 0 5 7 1 0 0 0 0 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 24 2 0 0 0 0 15 25 2 0 0 0 0 15 26 1 0 0 0 0 16 22 1 1 0 0 0 17 23 1 1 0 0 0 18 26 1 1 0 0 0 19 7 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 1 0 0 0 21 23 1 1 0 0 0 22 3 1 1 0 0 0 23 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.25
Volume:	390.6
LogP:	4.474
LogD:	4.6
LogS:	-4.595
# Rotatable Bonds:	4
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.578
Fsp3:	0.826
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	3.161198037560098e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.427
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	70.07061004638672%
Volume Distribution (VD):	1.7
Pgp-substrate:	27.295801162719727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.333
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	2.969
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.71
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.705
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.989
Carcinogencity:	0.315
Eye Corrosion:	0.989
Eye Irritation:	0.933
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC474971

Natural Product ID:	NPC474971
*Common Name:**	Stereonsteroid B
IUPAC Name:	[(3S,5S,8S,9S,10R,13R,14S,17R)-17-ethenyl-10-formyl-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	KFBNAACJXKPXPM-GCIAHNQISA-N
Standard InCHI:	InChI=1S/C23H34O3/c1-4-16-6-8-20-19-7-5-17-13-18(26-15(2)25)9-12-23(17,14-24)21(19)10-11-22(16,20)3/h4,14,16-21H,1,5-13H2,2-3H3/t16-,17-,18-,19-,20-,21-,22+,23+/m0/s1
SMILES:	C=C[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C=O)CC[C@@H](C2)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490531
PubChem CID:	11660453
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO33076	stereonephthya crystalliana	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16441077]

☑ 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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[479021]
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.6	ug.mL-1	PMID[479021]

☑ 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 NPC474971 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	206
0.1-0.2	1647
0.2-0.3	7368
0.3-0.4	15580
0.4-0.5	6095
0.5-0.6	6088
0.6-0.7	4497
0.7-0.8	1172
0.8-0.85	41
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.869	High Similarity	NPC475509
0.8588	High Similarity	NPC98270
0.8488	Intermediate Similarity	NPC264127
0.8488	Intermediate Similarity	NPC471042
0.8353	Intermediate Similarity	NPC471037
0.8315	Intermediate Similarity	NPC328141
0.8313	Intermediate Similarity	NPC471475
0.8295	Intermediate Similarity	NPC4309
0.8295	Intermediate Similarity	NPC97884
0.8295	Intermediate Similarity	NPC472220
0.8276	Intermediate Similarity	NPC12774
0.825	Intermediate Similarity	NPC279241
0.8242	Intermediate Similarity	NPC303863
0.8222	Intermediate Similarity	NPC218301
0.8222	Intermediate Similarity	NPC470230
0.8193	Intermediate Similarity	NPC63020
0.8182	Intermediate Similarity	NPC33768
0.8161	Intermediate Similarity	NPC264317
0.8161	Intermediate Similarity	NPC294438
0.8152	Intermediate Similarity	NPC84383
0.814	Intermediate Similarity	NPC170862
0.8132	Intermediate Similarity	NPC474185
0.8132	Intermediate Similarity	NPC294263
0.8111	Intermediate Similarity	NPC169933
0.8111	Intermediate Similarity	NPC471896
0.8095	Intermediate Similarity	NPC47808
0.8095	Intermediate Similarity	NPC305835
0.809	Intermediate Similarity	NPC224145
0.8068	Intermediate Similarity	NPC2783
0.8065	Intermediate Similarity	NPC471039
0.8046	Intermediate Similarity	NPC264665
0.8046	Intermediate Similarity	NPC74595
0.8043	Intermediate Similarity	NPC269729
0.8043	Intermediate Similarity	NPC471040
0.8022	Intermediate Similarity	NPC160506
0.8022	Intermediate Similarity	NPC471901
0.8022	Intermediate Similarity	NPC475416
0.8	Intermediate Similarity	NPC206735
0.8	Intermediate Similarity	NPC474679
0.8	Intermediate Similarity	NPC11611
0.8	Intermediate Similarity	NPC170038
0.8	Intermediate Similarity	NPC471043
0.8	Intermediate Similarity	NPC164999
0.8	Intermediate Similarity	NPC304194
0.798	Intermediate Similarity	NPC230888
0.7979	Intermediate Similarity	NPC469810
0.7978	Intermediate Similarity	NPC269360
0.7978	Intermediate Similarity	NPC474684
0.7978	Intermediate Similarity	NPC264005
0.7978	Intermediate Similarity	NPC142361
0.7957	Intermediate Similarity	NPC279974
0.7957	Intermediate Similarity	NPC98639
0.7957	Intermediate Similarity	NPC470229
0.7957	Intermediate Similarity	NPC274417
0.7955	Intermediate Similarity	NPC470223
0.7952	Intermediate Similarity	NPC92489
0.7952	Intermediate Similarity	NPC471046
0.7935	Intermediate Similarity	NPC224060
0.7935	Intermediate Similarity	NPC287118
0.7935	Intermediate Similarity	NPC79117
0.7935	Intermediate Similarity	NPC471902
0.7935	Intermediate Similarity	NPC473690
0.7935	Intermediate Similarity	NPC470224
0.7935	Intermediate Similarity	NPC244356
0.7931	Intermediate Similarity	NPC245866
0.7931	Intermediate Similarity	NPC139206
0.7917	Intermediate Similarity	NPC310981
0.7912	Intermediate Similarity	NPC474842
0.7912	Intermediate Similarity	NPC475965
0.7912	Intermediate Similarity	NPC111585
0.7912	Intermediate Similarity	NPC148414
0.7912	Intermediate Similarity	NPC175628
0.7895	Intermediate Similarity	NPC477854
0.7895	Intermediate Similarity	NPC472028
0.7889	Intermediate Similarity	NPC16377
0.7889	Intermediate Similarity	NPC474719
0.7889	Intermediate Similarity	NPC146937
0.7889	Intermediate Similarity	NPC28227
0.7889	Intermediate Similarity	NPC471900
0.7882	Intermediate Similarity	NPC118987
0.7882	Intermediate Similarity	NPC44083
0.7882	Intermediate Similarity	NPC153987
0.7872	Intermediate Similarity	NPC327788
0.7872	Intermediate Similarity	NPC29410
0.7872	Intermediate Similarity	NPC329910
0.7872	Intermediate Similarity	NPC122324
0.7872	Intermediate Similarity	NPC151725
0.7872	Intermediate Similarity	NPC106425
0.7872	Intermediate Similarity	NPC200054
0.7872	Intermediate Similarity	NPC111684
0.7872	Intermediate Similarity	NPC58052
0.7865	Intermediate Similarity	NPC472505
0.7865	Intermediate Similarity	NPC10005
0.7865	Intermediate Similarity	NPC91525
0.7865	Intermediate Similarity	NPC98236
0.7865	Intermediate Similarity	NPC9892
0.7865	Intermediate Similarity	NPC329943
0.7865	Intermediate Similarity	NPC195640
0.7865	Intermediate Similarity	NPC155011
0.7865	Intermediate Similarity	NPC269396
0.7857	Intermediate Similarity	NPC66105
0.7857	Intermediate Similarity	NPC29705
0.7849	Intermediate Similarity	NPC272635
0.7849	Intermediate Similarity	NPC169751
0.7849	Intermediate Similarity	NPC294266
0.7849	Intermediate Similarity	NPC475118
0.7841	Intermediate Similarity	NPC109512
0.7841	Intermediate Similarity	NPC263974
0.7841	Intermediate Similarity	NPC100391
0.7826	Intermediate Similarity	NPC26888
0.7826	Intermediate Similarity	NPC250753
0.7816	Intermediate Similarity	NPC142683
0.7816	Intermediate Similarity	NPC100297
0.7812	Intermediate Similarity	NPC94906
0.7802	Intermediate Similarity	NPC247312
0.7802	Intermediate Similarity	NPC116146
0.7802	Intermediate Similarity	NPC128496
0.7802	Intermediate Similarity	NPC271974
0.7802	Intermediate Similarity	NPC57954
0.7802	Intermediate Similarity	NPC24772
0.7802	Intermediate Similarity	NPC474704
0.7802	Intermediate Similarity	NPC474889
0.7802	Intermediate Similarity	NPC213832
0.7802	Intermediate Similarity	NPC475921
0.7802	Intermediate Similarity	NPC220498
0.7789	Intermediate Similarity	NPC292133
0.7789	Intermediate Similarity	NPC476768
0.7789	Intermediate Similarity	NPC96839
0.7789	Intermediate Similarity	NPC23680
0.7778	Intermediate Similarity	NPC4643
0.7778	Intermediate Similarity	NPC159046
0.7778	Intermediate Similarity	NPC233836
0.7778	Intermediate Similarity	NPC57469
0.7778	Intermediate Similarity	NPC46912
0.7778	Intermediate Similarity	NPC187376
0.7778	Intermediate Similarity	NPC134197
0.7778	Intermediate Similarity	NPC162107
0.7766	Intermediate Similarity	NPC288906
0.7766	Intermediate Similarity	NPC469599
0.7766	Intermediate Similarity	NPC470232
0.7766	Intermediate Similarity	NPC205173
0.7766	Intermediate Similarity	NPC266431
0.7766	Intermediate Similarity	NPC263135
0.7765	Intermediate Similarity	NPC185465
0.7753	Intermediate Similarity	NPC323765
0.7742	Intermediate Similarity	NPC477855
0.7742	Intermediate Similarity	NPC475061
0.7738	Intermediate Similarity	NPC246445
0.7738	Intermediate Similarity	NPC104806
0.7732	Intermediate Similarity	NPC477052
0.7732	Intermediate Similarity	NPC75941
0.7732	Intermediate Similarity	NPC477051
0.7732	Intermediate Similarity	NPC477053
0.7727	Intermediate Similarity	NPC473742
0.7727	Intermediate Similarity	NPC475726
0.7727	Intermediate Similarity	NPC472743
0.7727	Intermediate Similarity	NPC5280
0.7723	Intermediate Similarity	NPC257082
0.7723	Intermediate Similarity	NPC285298
0.7717	Intermediate Similarity	NPC20388
0.7711	Intermediate Similarity	NPC167702
0.7711	Intermediate Similarity	NPC280026
0.7708	Intermediate Similarity	NPC119036
0.7708	Intermediate Similarity	NPC38296
0.7708	Intermediate Similarity	NPC471038
0.7708	Intermediate Similarity	NPC469986
0.7708	Intermediate Similarity	NPC162459
0.7708	Intermediate Similarity	NPC28864
0.7708	Intermediate Similarity	NPC38471
0.7708	Intermediate Similarity	NPC98837
0.7708	Intermediate Similarity	NPC20479
0.7701	Intermediate Similarity	NPC164210
0.7692	Intermediate Similarity	NPC474845
0.7692	Intermediate Similarity	NPC472739
0.7692	Intermediate Similarity	NPC80335
0.7692	Intermediate Similarity	NPC255176
0.7684	Intermediate Similarity	NPC219353
0.7684	Intermediate Similarity	NPC234564
0.7684	Intermediate Similarity	NPC160056
0.7684	Intermediate Similarity	NPC104568
0.7684	Intermediate Similarity	NPC477853
0.7684	Intermediate Similarity	NPC13949
0.7674	Intermediate Similarity	NPC320144
0.7674	Intermediate Similarity	NPC192744
0.7667	Intermediate Similarity	NPC55309
0.7667	Intermediate Similarity	NPC28252
0.7667	Intermediate Similarity	NPC325594
0.7667	Intermediate Similarity	NPC80590
0.7667	Intermediate Similarity	NPC70661
0.7667	Intermediate Similarity	NPC94755
0.766	Intermediate Similarity	NPC473280
0.766	Intermediate Similarity	NPC470385
0.766	Intermediate Similarity	NPC47853
0.766	Intermediate Similarity	NPC473435
0.766	Intermediate Similarity	NPC470386
0.766	Intermediate Similarity	NPC159410
0.766	Intermediate Similarity	NPC471078
0.766	Intermediate Similarity	NPC473431
0.7653	Intermediate Similarity	NPC124544
0.7653	Intermediate Similarity	NPC477054

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 NPC474971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2032
0.2-0.3	4270
0.3-0.4	1777
0.4-0.5	456
0.5-0.6	187
0.6-0.7	163
0.7-0.8	83
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8161	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD8035	Phase 2
0.8022	Intermediate Similarity	NPD8034	Phase 2
0.7889	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD5330	Approved
0.7865	Intermediate Similarity	NPD6409	Approved
0.7865	Intermediate Similarity	NPD7146	Approved
0.7865	Intermediate Similarity	NPD6684	Approved
0.7865	Intermediate Similarity	NPD7521	Approved
0.7865	Intermediate Similarity	NPD7334	Approved
0.7742	Intermediate Similarity	NPD6399	Phase 3
0.7711	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD6672	Approved
0.7692	Intermediate Similarity	NPD6903	Approved
0.7683	Intermediate Similarity	NPD5777	Approved
0.7634	Intermediate Similarity	NPD6079	Approved
0.7609	Intermediate Similarity	NPD5328	Approved
0.7529	Intermediate Similarity	NPD6117	Approved
0.7473	Intermediate Similarity	NPD6098	Approved
0.7451	Intermediate Similarity	NPD6899	Approved
0.7451	Intermediate Similarity	NPD6881	Approved
0.7444	Intermediate Similarity	NPD4786	Approved
0.7442	Intermediate Similarity	NPD6116	Phase 1
0.7426	Intermediate Similarity	NPD6675	Approved
0.7426	Intermediate Similarity	NPD7128	Approved
0.7426	Intermediate Similarity	NPD6402	Approved
0.7426	Intermediate Similarity	NPD5739	Approved
0.7391	Intermediate Similarity	NPD3573	Approved
0.7356	Intermediate Similarity	NPD6114	Approved
0.7356	Intermediate Similarity	NPD6118	Approved
0.7356	Intermediate Similarity	NPD6115	Approved
0.7356	Intermediate Similarity	NPD6697	Approved
0.7353	Intermediate Similarity	NPD5697	Approved
0.732	Intermediate Similarity	NPD4697	Phase 3
0.7308	Intermediate Similarity	NPD7290	Approved
0.7308	Intermediate Similarity	NPD7102	Approved
0.7308	Intermediate Similarity	NPD6883	Approved
0.7292	Intermediate Similarity	NPD7748	Approved
0.7292	Intermediate Similarity	NPD7900	Approved
0.7292	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7320	Approved
0.7282	Intermediate Similarity	NPD6011	Approved
0.7262	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6008	Approved
0.7238	Intermediate Similarity	NPD6617	Approved
0.7238	Intermediate Similarity	NPD6869	Approved
0.7238	Intermediate Similarity	NPD6650	Approved
0.7238	Intermediate Similarity	NPD6847	Approved
0.7238	Intermediate Similarity	NPD6649	Approved
0.7238	Intermediate Similarity	NPD8130	Phase 1
0.7234	Intermediate Similarity	NPD6673	Approved
0.7234	Intermediate Similarity	NPD6080	Approved
0.7234	Intermediate Similarity	NPD6904	Approved
0.7222	Intermediate Similarity	NPD3667	Approved
0.7216	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD6012	Approved
0.7212	Intermediate Similarity	NPD6013	Approved
0.7212	Intermediate Similarity	NPD6014	Approved
0.7212	Intermediate Similarity	NPD6373	Approved
0.7209	Intermediate Similarity	NPD3702	Approved
0.7184	Intermediate Similarity	NPD5701	Approved
0.7172	Intermediate Similarity	NPD7638	Approved
0.717	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5208	Approved
0.71	Intermediate Similarity	NPD7640	Approved
0.71	Intermediate Similarity	NPD7639	Approved
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD7515	Phase 2
0.7075	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7071	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD5173	Approved
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7024	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3703	Phase 2
0.6979	Remote Similarity	NPD5207	Approved
0.6972	Remote Similarity	NPD6868	Approved
0.6939	Remote Similarity	NPD6001	Approved
0.6931	Remote Similarity	NPD5286	Approved
0.6931	Remote Similarity	NPD4696	Approved
0.6931	Remote Similarity	NPD5285	Approved
0.6907	Remote Similarity	NPD5693	Phase 1
0.6907	Remote Similarity	NPD6050	Approved
0.6907	Remote Similarity	NPD5694	Approved
0.6907	Remote Similarity	NPD6411	Approved
0.6905	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5360	Phase 3
0.69	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD3665	Phase 1
0.6882	Remote Similarity	NPD3666	Approved
0.6882	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD6051	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.6867	Remote Similarity	NPD4224	Phase 2
0.6863	Remote Similarity	NPD5223	Approved
0.686	Remote Similarity	NPD6081	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6335	Approved
0.6837	Remote Similarity	NPD4202	Approved
0.6832	Remote Similarity	NPD5696	Approved
0.6813	Remote Similarity	NPD7525	Registered
0.6804	Remote Similarity	NPD5692	Phase 3
0.6796	Remote Similarity	NPD5226	Approved
0.6796	Remote Similarity	NPD5211	Phase 2
0.6796	Remote Similarity	NPD4633	Approved
0.6796	Remote Similarity	NPD5224	Approved
0.6796	Remote Similarity	NPD5225	Approved
0.6789	Remote Similarity	NPD4632	Approved
0.6786	Remote Similarity	NPD7100	Approved
0.6786	Remote Similarity	NPD7101	Approved
0.6765	Remote Similarity	NPD4700	Approved
0.6757	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD4789	Approved
0.6744	Remote Similarity	NPD4245	Approved
0.6744	Remote Similarity	NPD4244	Approved
0.6731	Remote Similarity	NPD5175	Approved
0.6731	Remote Similarity	NPD5174	Approved
0.6724	Remote Similarity	NPD7507	Approved
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD6313	Approved
0.6696	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD1694	Approved
0.6632	Remote Similarity	NPD5329	Approved
0.6629	Remote Similarity	NPD6942	Approved
0.6629	Remote Similarity	NPD7339	Approved
0.6628	Remote Similarity	NPD3698	Phase 2
0.6607	Remote Similarity	NPD7115	Discovery
0.6607	Remote Similarity	NPD6009	Approved
0.6593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6319	Approved
0.6571	Remote Similarity	NPD4754	Approved
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6562	Remote Similarity	NPD5279	Phase 3
0.6555	Remote Similarity	NPD7319	Approved
0.6552	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD4747	Approved
0.6548	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4753	Phase 2
0.6526	Remote Similarity	NPD4197	Approved
0.6522	Remote Similarity	NPD6909	Approved
0.6522	Remote Similarity	NPD5983	Phase 2
0.6522	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6908	Approved
0.6496	Remote Similarity	NPD7492	Approved
0.6486	Remote Similarity	NPD6858	Approved
0.6486	Remote Similarity	NPD7094	Approved
0.6486	Remote Similarity	NPD8133	Approved
0.6481	Remote Similarity	NPD5168	Approved
0.6481	Remote Similarity	NPD4730	Approved
0.6481	Remote Similarity	NPD4729	Approved
0.6477	Remote Similarity	NPD4758	Discontinued
0.6476	Remote Similarity	NPD7632	Discontinued
0.6471	Remote Similarity	NPD7736	Approved
0.6452	Remote Similarity	NPD5368	Approved
0.6449	Remote Similarity	NPD4768	Approved
0.6449	Remote Similarity	NPD4767	Approved
0.6441	Remote Similarity	NPD6336	Discontinued
0.6441	Remote Similarity	NPD6616	Approved
0.6437	Remote Similarity	NPD4137	Phase 3
0.6435	Remote Similarity	NPD6054	Approved
0.6415	Remote Similarity	NPD6052	Approved
0.6413	Remote Similarity	NPD3671	Phase 1
0.64	Remote Similarity	NPD7637	Suspended
0.6392	Remote Similarity	NPD4690	Approved
0.6392	Remote Similarity	NPD4138	Approved
0.6392	Remote Similarity	NPD4688	Approved
0.6392	Remote Similarity	NPD4693	Phase 3
0.6392	Remote Similarity	NPD5205	Approved
0.6392	Remote Similarity	NPD5690	Phase 2
0.6392	Remote Similarity	NPD4689	Approved
0.6389	Remote Similarity	NPD6614	Approved
0.6387	Remote Similarity	NPD7078	Approved
0.6374	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5654	Approved
0.6373	Remote Similarity	NPD5210	Approved
0.6373	Remote Similarity	NPD4629	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD5169	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