NPASS Compound

Natural Product: NPC528067

Natural Product ID	NPC528067
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{S})-2-(3,4-dihydroxyphenyl)-4-[(2~{R},3~{S})-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[4,5-dihydroxy-2-[(2~{R},3~{S})-3,5,7-trihydroxychroman-2-yl]phenyl]chromane-3,5,7-triol
IUPAC Name	(2~{S},3~{S},4~{S})-2-(3,4-dihydroxyphenyl)-4-[(2~{R},3~{S})-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[4,5-dihydroxy-2-[(2~{R},3~{S})-3,5,7-trihydroxychroman-2-yl]phenyl]chromane-3,5,7-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 101109 0 0 0 0 0 0 0 0999 V2000 9.2414 3.5249 0.5219 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1952 2.6507 0.2607 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5032 1.3482 -0.0652 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5009 0.4313 -0.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8676 -0.8600 -0.6567 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1727 0.8290 -0.2780 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 -0.1963 -0.5760 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 0.2138 -0.5095 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1522 -0.0640 -1.7631 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4292 1.5816 -0.0433 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5944 1.6422 1.1906 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2043 1.6495 2.4322 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5027 1.7063 3.6160 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1545 1.7116 4.8515 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1239 1.7592 3.5779 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3347 1.8192 4.7307 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5087 1.7524 2.3446 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 1.6949 1.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5200 1.6858 -0.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2270 2.8459 -0.8157 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6137 4.0513 -0.2377 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4287 2.7788 -2.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7992 1.5671 -2.5683 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4671 1.5798 -3.8062 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5238 0.3805 -1.9218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1332 0.4803 -0.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4225 -0.6944 -0.0446 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3856 -1.9401 -0.6559 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2047 -2.9567 0.4217 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7554 -2.7021 1.3979 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0138 -3.5564 2.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2723 -4.7297 2.5033 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5427 -5.5899 3.5623 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6816 -5.0030 1.5509 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4060 -6.1638 1.6293 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9183 -4.1196 0.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6606 -2.1050 -1.7105 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8144 -2.5843 -1.0809 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9388 -0.8923 -2.5358 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3434 -0.9240 -2.9540 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6393 -1.3962 -4.2270 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6355 -1.8276 -5.0820 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9399 -1.4490 -4.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0078 -1.0306 -3.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3073 -1.0959 -4.3502 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7273 -0.5680 -2.6255 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4007 -0.5248 -2.1952 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2036 -0.0451 -0.9292 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9745 1.0457 -0.4080 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0709 0.9845 1.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8639 2.1442 1.7846 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 2.1842 3.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2207 1.0397 3.8781 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3016 1.0350 5.2705 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4314 -0.1307 3.1748 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7183 -1.2719 3.9132 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3566 -0.1524 1.7914 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3428 1.1568 -0.9911 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3777 2.2027 -1.9343 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7888 -0.1006 -1.6976 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5283 2.4574 0.0866 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8481 2.1094 0.0415 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8727 3.0166 0.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1400 4.4479 0.8980 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5592 1.0578 -0.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5469 -0.9925 -1.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4336 -0.6036 -1.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3902 -1.0650 0.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2178 -0.4996 0.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4023 -1.0010 -1.9657 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7806 2.0611 -0.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2838 1.6085 2.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1073 2.0429 4.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2878 0.9552 5.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5668 1.7937 2.3058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5003 4.4952 -0.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6443 3.7221 -2.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9457 1.1657 -4.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4087 -2.1361 -1.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3476 -1.7796 1.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7718 -3.3525 3.2042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3380 -6.1934 3.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0339 -7.0279 1.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6621 -4.3067 -0.2489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3119 -2.9722 -2.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2172 -3.3484 -1.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3233 -0.9876 -3.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5975 -2.7897 -5.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1271 -1.8267 -5.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9227 -1.7962 -3.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3812 1.9537 -0.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6339 3.0689 1.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7718 3.0930 3.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1568 1.9392 5.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2033 -1.1829 4.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5219 -1.0653 1.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0753 1.3536 -0.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3452 2.4875 -1.9837 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0285 -0.8656 -0.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7343 0.1337 -2.2553 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6372 4.0267 0.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 4 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 13 15 2 0 15 16 1 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 2 0 28 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 40 41 2 0 41 42 1 0 41 43 1 0 43 44 2 0 44 45 1 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 53 55 1 0 55 56 1 0 55 57 2 0 49 58 1 0 58 59 1 0 58 60 1 0 10 61 1 0 61 62 1 0 62 63 2 0 63 2 1 0 62 6 1 0 18 11 1 0 26 19 1 0 36 29 1 0 47 40 1 0 57 50 1 0 39 25 1 0 60 46 1 0 1 64 1 0 3 65 1 0 5 66 1 0 7 67 1 0 7 68 1 0 8 69 1 1 9 70 1 0 10 71 1 6 12 72 1 0 14 73 1 0 16 74 1 0 17 75 1 0 21 76 1 0 22 77 1 0 24 78 1 0 28 79 1 6 30 80 1 0 31 81 1 0 33 82 1 0 35 83 1 0 36 84 1 0 37 85 1 6 38 86 1 0 39 87 1 6 42 88 1 0 43 89 1 0 45 90 1 0 49 91 1 1 51 92 1 0 52 93 1 0 54 94 1 0 56 95 1 0 57 96 1 0 58 97 1 1 59 98 1 0 60 99 1 0 60100 1 0 63101 1 0 M END

Standard InCHIKey	SKKJVAJWPVLPPD-JTGACUGOSA-N
Standard InCHI	InChI=1S/C45H38O18/c46-17-7-24(49)20-11-34(59)43(61-35(20)8-17)19-10-29(54)28(53)9-18(19)36-30(55)14-32(57)38-39(40(60)42(63-45(36)38)16-2-4-23(48)27(52)6-16)37-31(56)13-25(50)21-12-33(58)41(62-44(21)37)15-1-3-22(47)26(51)5-15/h1-10,13-14,33-34,39-43,46-60H,11-12H2/t33-,34-,39-,40-,41+,42-,43+/m0/s1
SMILES	OC1=CC(O)=C2C[C@H](O)[C@@H](C3=CC(O)=C(O)C=C3C3=C(O)C=C(O)C4=C3O[C@@H](C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H]4C3=C(O)C=C(O)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H](O)C4)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	866.21	Volume:	820.635 ? Van der Waals volume.
Dense:	1.056	LogP:	0.98 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.173 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.843 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	51.0
TPSA:	331.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	15.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.488	Fsp³:	0.2
MCE-18:	193.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.782	Fluc inhibitor:	0.158 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.736 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.642 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.592	Promiscuous compounds:	0.182

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.685	MDCK Permeability:	-4.752
Pgp-inhibitor:	0.0	Pgp-substrate:	0.079
PAMPA:	0.649 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.982
Plasma Protein Binding (PPB):	90.551%	Volume Distribution (VD):	0.238
Fu:	11.838% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.015
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.05	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.951
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.631

Half-life (T1/2):

7.125

ADMET: Toxicity

hERG Blockers:	0.106	hERG Blockers (10um):	0.912
Human Hepatotoxicity (H-HT):	0.933	Drug-induced Liver Injury (DILI):	0.36
AMES Toxicity:	0.589	Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.688	Respiratory Toxicity:	0.523
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.056
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.979
BCF:	1.096 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.815 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.979 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.337 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11804	Potentilla erecta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11804	Potentilla erecta	Species	Rosaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC528067 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	23828
0.1-0.2	24230
0.2-0.3	1592
0.3-0.4	98
0.4-0.5	42
0.5-0.6	36
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7397	Intermediate Similarity	NPC58190
0.7397	Intermediate Similarity	NPC108811
0.7397	Intermediate Similarity	NPC170103
0.7397	Intermediate Similarity	NPC236202
0.7397	Intermediate Similarity	NPC262911
0.7397	Intermediate Similarity	NPC202742
0.7297	Intermediate Similarity	NPC246202
0.7297	Intermediate Similarity	NPC224161
0.7297	Intermediate Similarity	NPC46335
0.7297	Intermediate Similarity	NPC279406
0.7297	Intermediate Similarity	NPC486519
0.6667	Remote Similarity	NPC278548
0.6456	Remote Similarity	NPC313116
0.6456	Remote Similarity	NPC603340
0.642	Remote Similarity	NPC226809
0.6296	Remote Similarity	NPC70409
0.6296	Remote Similarity	NPC204770
0.6296	Remote Similarity	NPC600551
0.6296	Remote Similarity	NPC601980
0.6296	Remote Similarity	NPC602065
0.6296	Remote Similarity	NPC611024
0.6234	Remote Similarity	NPC96576
0.6145	Remote Similarity	NPC600630
0.6145	Remote Similarity	NPC607896
0.6145	Remote Similarity	NPC611369
0.6	Remote Similarity	NPC294558
0.6	Remote Similarity	NPC86630
0.6	Remote Similarity	NPC18185
0.6	Remote Similarity	NPC263940
0.5955	Remote Similarity	NPC147743
0.5955	Remote Similarity	NPC4809
0.5955	Remote Similarity	NPC73517
0.5934	Remote Similarity	NPC106601
0.5934	Remote Similarity	NPC151474
0.587	Remote Similarity	NPC212614
0.587	Remote Similarity	NPC205613
0.5833	Remote Similarity	NPC261619
0.5833	Remote Similarity	NPC61477
0.5833	Remote Similarity	NPC78770
0.5833	Remote Similarity	NPC219876
0.5833	Remote Similarity	NPC126029
0.5833	Remote Similarity	NPC15658
0.5833	Remote Similarity	NPC211561
0.5684	Remote Similarity	NPC159526
0.5679	Remote Similarity	NPC601999
0.5647	Remote Similarity	NPC601997
0.5647	Remote Similarity	NPC609211
0.5647	Remote Similarity	NPC610665
0.5517	Remote Similarity	NPC302549
0.5455	Remote Similarity	NPC178054
0.5393	Remote Similarity	NPC20050
0.5357	Remote Similarity	NPC184245
0.5357	Remote Similarity	NPC187801
0.5357	Remote Similarity	NPC610920
0.5333	Remote Similarity	NPC306267
0.5275	Remote Similarity	NPC135021
0.5269	Remote Similarity	NPC9309
0.5263	Remote Similarity	NPC78074
0.5263	Remote Similarity	NPC478340
0.5116	Remote Similarity	NPC28440
0.5056	Remote Similarity	NPC272552
0.5056	Remote Similarity	NPC226108
0.5056	Remote Similarity	NPC322899
0.5052	Remote Similarity	NPC478337
0.5052	Remote Similarity	NPC478338

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC528067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5364
0.1-0.2	3766
0.2-0.3	16
0.3-0.4	2
0.4-0.5	0
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
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
0.5833	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1613	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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